Su, Y.-L.; Tram, L.; Wherritt, D.; Arman, H.; Griffith, W. P.; Doyle, M. P.* α-Amino Radical-Mediated Diverse Difunctionalization of Alkenes: Construction of C-C, C-N and C-S Bonds. ACS Catal. 2020, 10, 13682−13687. DOI: 10.1021/acscatal.0c04243


Su, Y.-L.; Liu, G.-X.; Liu, J.-W.; Tram, L.; Qiu, H.;* Doyle, M. P.* Radical-Mediated Strategies for the Functionalization of Alkenes with Diazo Compounds. J. Am. Chem. Soc. 2020, 142, 13846-13855. DOI:


Dong, K.; Xu, X.; Doyle, M. P. “Copper(I)-catalyzed highly enantioselective [3+3]-cycloaddition of γ-alkyl enoldiazoacetates with nitronesOrg. Chem. Front. 2020, 7, 1653 –1657. DOI: 10.1039/D0QO00539H


Marichev, K. O.; Wang, K.; Greco, N.; Dong, K.; Chen, J.;  Lei, J.;  Doyle, M. P. Strain-Induced Nucleophilic Ring Opening of Donor-Acceptor Cyclopropenes for Synthesis of Monosubstituted Succinic Acid Derivatives. Chem. Eur. J. Accepted.  DOI: 10.1002/chem.202003427


Wang, R.; Marichev, K. O.; Dong, K.; Jensen, J. A.; Doyle, M. P. Chiral 3‑Acylglutaric Acid Derivatives from Strain-Induced Nucleophilic Retro-Claisen Ring-Opening Reactions. J. Org. Chem. 2020, 85, 9475–9490. DOI: 10.1021/acs.joc.0c01176


Zheng, H.; Dong, K.; Wherritt, D.; Arman, H.; Doyle, M. P. “Brønsted Acid Catalyzed Friedel-Crafts-type Coupling and Dedinitrogenation Reactions of Vinyldiazo Compounds” Angew. Chem. Int. Ed. 2020, 59, 13613–13617. DOI: 10.1002/ange.202004328


Su, Y.-L.; De Angelis, L.; Tram, L.; Yu, Y.; Doyle, M. P. “Catalytic Oxidative Cleavage Reactions of Arylalkenes by tert-Butyl Hydroperoxide – A Mechanistic Assessment” J. Org. Chem. 2020, 85, 5, 3728–3741. DOI: 10.1021/acs.joc.9b03346


Marichev, K. O.; Dong, K.; Massey, L. A.; Deng, Y.; De Angelis, L.; Wang, K.; Arman, H.; Doyle, M. P. “Chiral donor−acceptor azetines as powerful reactants for synthesis of amino acid derivatives” Nature Commun. 2019, 10, 5328. DOI: 10.1038/s41467-019-13326-8.

Behind the Paper Post in Nature Research Community.

Highlighted in Synfacts 2020, 16 (04), 0480. DOI: 10.1055/s-0039-1690061.


Neff, R. K., Su, Y.-L., Liu, S., Rosado, M., Zhang, X., Doyle, M. P. “Generation of Halomethyl Radicals by Halogen Atom Abstraction and Their Addition Reactions with Alkenes” J. Am. Chem. Soc. 2019, 141, 1644316450. DOI: 10.1021/jacs.9b05921


Marichev, K. O.; Wang, K.; Dong, K.; Greco, N.; Massey, L. A.; Deng, Y.; Arman, H.; Doyle, M. P. “ Synthesis of Chiral Tetrasubstituted Azetidines from Donor-Acceptor Azetines via Asymmetric Copper(I)-Catalyzed Imido-Ylide [3+1]-Cycloaddition with Metallo-Enolcarbenes” Angew. Chem. Int. Ed. 2019, 58, 16188–16192. DOI: 10.1002/anie.201909929.

Highlighted in Synfacts 2019, 15 (12), 1393. DOI: 10.1055/s-0039-1691111


Su, Y.-L.; De Angelis, L.; Doyle, M. P. “Discussion Addendum for: Allylic Oxidation Catalyzed by Dirhodium(II) Tetrakis[e-caprolactamate] of tert-Butyldimethylsilyl-protected trans-Dehydroandrosterone” Org. Synth. 2019, 96, 300-311. DOI: 10.15227/orgsyn.096.0300


Dong, K.; Marichev, K. O.; Doyle, M. P. “The Role of Donor-Acceptor Cyclopropenes in Metal Carbene Reactions. Conversion of E-Substituted Enoldiazoacetates to Z-Substituted Metallo-Enolcarbenes” Organometallics 2019, 38, 4043–4050. DOI: 10.1021/acs.organomet.9b00427


Zheng, H.; Doyle, M. P. “Catalytic Desymmetric Cycloaddition of Diaziridines with Metalloenolcarbenes. The Role of Donor-Acceptor Cyclopropenes” Angew. Chem. Int. Ed. 2019, 58, 10343-10346. DOI: 10.1002/anie.201906754


Dong, K.; Marichev, K. O.; Xu, X.; Doyle, M. P. “High Stereocontrol in the Preparation of Silyl-Protected γ-Substituted Enoldiazoacetates” Synlett 2019, 30, 1457-1461. DOI: 10.1055/s-0037-1611865


Marichev, K. O.; Doyle, M. P. “Catalytic asymmetric cycloaddition reactions of enoldiazo compounds” Org. & Biomol. Chem. 201917, 4183 – 4195. DOI: 10.1039/C9OB00478E


Adly, F. G.; Marichev, K. O.; Jensen, J. A.; Arman, H.; Doyle, M. P. “Enoldiazosulfones for Highly Enantioselective [3+3]-Cycloaddition Reactions with Nitrones Catalyzed by Copper(I) with Chiral BOX Ligands” Org. Lett. 2019, 21, 40 – 44. DOI: 10.1021/acs.orglett.8b03421


Qiu, H.; Arman, H.; Hu, W.; Doyle, M. P. “Intramolecular cycloaddition/ rearrangement cascade from gold(III)-catalysed reactions of propargyl aryldiazoesters with cinnamyl imines” Chem. Commun. 201854, 12828 – 12831. DOI: 10.1039/C8CC07885H


Marichev, K. O.; Adly, F. G.; Carranco, A. M.; Garcia, E. C.; Arman, H.; Doyle, M. P. “Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds” ACS Catal. 2018, 8, 10392 – 10400. DOI: 10.1021/acscatal.8b03391


Dong, K.; Pei, C.; Zeng, Q.; Wei, H; Doyle, M. P.; Xu, X. “Selective C(sp3)–H Bond Insertion in Carbene/Alkyne Metathesis Reactions. Enantioselective Construction of Dihydroindoles” ACS Catal. 2018, 8, 9543–9549. (DOI: 10.1021/acscatal.8b02822)


Sha, Q.; Wang, J.; Doyle, M. P. “Synthesis of 1H-Pyrrol-3(2H)-ones via Three-Component Reactions of 2,3-Diketo Esters, Amines, and Ketones” J. Org. Chem. 2018, 83, 11288-11297. (DOI: 10.1021/acs.joc.8b01887)


Marichev, K. O.; Wang, Y.; Carranco, A. M.; Garcia, E. C.; Yu, Z.-X.; Doyle, M. P. “Rhodium(II)-Catalysed Generation of Cycloprop-1-en-1-yl Ketones and Their Rearrangement to 5-Aryl-2-siloxyfurans” Chem. Commun. 2018, 54, 9513-9516. (DOI: 10.1039/C8CC05623D)


Cheng, Q.-Q.; Massey, L. A.; Willett, B. S.; Deng, Y.; Arman, H.; Doyle, M. P. “Copper-Catalyzed Formal [4+2]-Cycloaddition of Enoldiazoimides with Sulfur Ylides” Angew. Chem. Int  Ed. 2018, 57, 10343-10346. (DOI: 10.1002/anie.201805323)


Mazzola, E. P.; Gutierrez, O.; Fraenkel, G. A.; Chow, A.; Doyle, M. P.; Mandler, M. D.; Dykstra, R.; Garg, D.; Ridge, C. D. “Unusually large scalar coupling between geminal protons in a saturated pyrimidine” Concepts Magn. Reson. Part A. 2016; 45A: e21424. (DOI: 10.1002/cmr.a.21424)


Yu, Y.; Sha, Q.; Cui, H.; Chandler, K. S.; Doyle, M.P. “Displacement of Dinitrogen by Oxygen. A Methodology for the Catalytic Conversion of Diazocarbonyl Compounds to Ketocarbonyl Compounds by 2,6-Dichloropyridine-N-oxide” Org. Lett. 2018, 20, 776-779. (DOI: 10.1021/acs.orglett.7b03912)


Cheng, Q.-Q.; Yu, Y.; Yedoyan, J.; Doyle, M.P. “Vinyldiazo Reagents and Metal Catalysts: A Versatile Toolkit for Heterocycle and Carbocycle Construction” ChemCatChem 2018, 488-496. (DOI: 10.1002/cctc.201701346)


Marichev, K.O.; Garcia, E.C.; Bhowmick, K.C.; Wherritt, D.J.; Arman, H.; and Doyle, M.P. “Highly Selective Acylation of Polyamines and Aminoglycosides by 5-acyl-5-phenyl-1,5-dihydro-4H-pyrazol-4-ones” Chem. Sci. 2017, 8, 7152–7159. (DOI: 10.1039/C7SC03184J)


Deng, Y.; Massey, L.A.; Rodriguez Núñez, Y.A.; Arman, H.; Doyle, M.P. “Catalytic Divergent [3+3]- and [3+2]-Cycloaddition by Discrimination Between Diazo Compounds” Angew. Chem. Int. Ed. 2017, 57, 12292–12296. (DOI:10.1002/anie.201706639)


Cheng, Q.-Q.; Deng, Y.; Lankelma, M.; Doyle, M.P. “Cycloaddition Reactions of Enoldiazo Compounds” Chem. Soc. Rev. 2017, 46, 5425-5443. (DOI: 10.1039/c7cs00324b)


Cheng, Q.-Q.; Lankelma, M.; Wherritt, D.; Arman, H.; Doyle, M.P. “Divergent Rhodium-Catalyzed Cyclization Reactions of Enoldiazoacetamides with Nitrosoarenes” J. Am. Chem. Soc. 2017, 139, 9839-9842. (DOI: 10.1021/jacs.7b05840)


Deng, Y.; Cheng, Q.-Q.; Doyle, M.P. “Asymmetric [3+3] Cycloaddition for Heterocycle Synthesis” Synlett 2017, 28, 1695-1706. (DOI: 10.1055/s-0036-1588453)


Yu, Y.; Humeidi, R.; Alleyn, J.R.; Doyle, M.P. “Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP” J. Org. Chem.2017, 82, 10732-10736. (DOI: 10.1021/acs.joc.7b01163)


Deng, Y.; Massey, L.A.; Zavalij, P.Y.; Doyle, M.P. “Catalytic Asymmetric [3+1]-Cycloaddition Reaction of Ylides with Electrophilic Metallo-Enolcarbene Intermediates” Angew. Chem. Int. Ed. 2017, 56, 7479-7483. (DOI: 10.1002/anie.201704069)


Marichev, K.O.; Ramey, J.T.; Arman, H.; Doyle, M.P. “Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates” Org. Lett. 2017, 19, 1306-1309. (DOI: 10.1021/acs.orglett.6b02965)


Duan, A.; Yu, P.; Liu, F.; Qiu, H.; Gu, F.L.; Doyle, M.P.; Houk, K.N. “Diazo Esters as Dienophiles in Intramolecular (4+2) Cycloadditions: Computational Explorations of Mechanism” J. Am. Chem. Soc. 2017, 139, 2766-2770. (DOI: 10.1021/jacs.6b12371)


Qiu, H.; Deng, Y.; Marichev, K.O.; Doyle, M.P. “Diverse Pathways in Catalytic Reactions of Propargyl Aryldiazoacetates. Selectivity Between Three Reaction Sites” J. Org. Chem. 2017, 82, 1584-1590. (DOI: 10.1021/acs.joc.6b02770)


Deng, Y.; Pei, C.; Arman, H.; Dong, K.; Xu, X.; Doyle, M.P. “Syntheses of Tetrahydropyridazine and Tetrahydro-1,2-diazepine Scaffolds through Cycloaddition Reactions of Azoalkenes with Enol Diazoacetates” Org. Lett. 2016, 18, 5884–5887. (DOI: 10.1021/acs.orglett.6b02965)


Deng, Y.; Jing, C.; Arman, H.; Doyle, M.P. “Reactivity and Selectivity in Catalytic Reactions of Enoldiazoacetamides. Assessment of Metal Carbenes as Intermediates” Organometal. 2016, 35, 3413-3420. (DOI: 10.1021/acs.organomet.6b00648)


Marichev, K.O.; Qiu, H.; Offield, A.C.; Arman, H.; Doyle, M.P. “Catalyst-free Rearrangement of Allenyl Aryldiazoacetates into 1,5-Dihydro-4H-pyrazol-4-ones” J. Org. Chem. 2016, 81, 9235-9246. (DOI: 10.1021/acs.joc.6b01833)


Jing, C.; Cheng, Q.-Q.; Deng, Y.; Arman, H.; Doyle, M.P. “Highly Regio- and Enantioselective Formal [3+2]-Annulation of Indoles with Electrophilic Enol Carbene Intermediates” Org. Lett. 2016, 18, 4550-4553. (DOI: 10.1021/acs.orglett.6b02192)


Deng, Y.; Yglesias, M.V.; Arman, H.; Doyle, M.P. “Catalytic Asymmetric Synthesis of Cyclopentyl β-Amino Esters by [3+2]-Cycloaddition of Enecarbamates with Electrophilic Metalloenolcarbene Intermediates” Angew. Chem. Int. Ed. 2016, 55, 10108-10112. (DOI: 10.1002/anie.20160543)


Cheng, Q.-Q.; Yedoyan, J.; Arman, H.; Doyle, M.P. “Dirhodium(II)-Catalyzed Annulation of Enoldiazoacetamides with α-Diazoketones: An Efficient and Highly Selective Approach to Fused and Bridged Ring System” Angew. Chem. Int. Ed. 2016, 55, 5573-5576. (cover story) (DOI: 10.1002/anie.201601260)


Deng, Y.; Doyle. M.P. “Versatile Donor-Acceptor Cyclopropenes in Metal Carbene Transformations” Isr. J. Chem. 2016, 56, 399-408. (DOI: 10.1002/ijch.201500083)


Qiu, H.; Srinivas, H.; Zavalij, P.; Doyle, M.P. “Unprecedented Intramolecular [4+2]-Cycloaddition Between a 1,3-Diene and a Diazo Ester” J. Am. Chem. Soc. 2016. 138, 1808-1811. (DOI: 10.1021/jacs.5b12877)


Cheng, Q.-Q.; Yedoyan, J.; Arman, H.; Doyle, M.P. “Copper-Catalyzed Divergent Addition Reactions of Enoldiazoacetamides with Nitrones” J. Am. Chem. Soc. 2016, 138, 44-47. (DOI: 10.1021/jacs.5b10860)


Deng, Y.; Qiu, H.; Srinivas, H.D.; Doyle, M.P. “Chiral Dirhodium(II) Catalysts for Selective Metal Carbene Reactions” Curr. Org. Chem. 2016, 20, 61-81. (DOI: 10.2174/1385272819666150714182732)


Sha, Q.; Arman, H.; Doyle, M.P. “Asymmetric Synthesis of 1H-Pyrrol-3(2H)-ones from 2,3-Diketoesters by Combination of Aldol Condensation with Benzilic Acid Rearrangement” Chem. Commun. 2016, 52, 108-111. (DOI: 10.1039/C5CC07780J)


Deng, Y.; Jing, C.; Zavalij, P.Y.; Doyle, M.P. “Hg(OTf)2 Catalyzed Intramolecular 1,4-Addition of Donor-acceptor Cyclopropenes to Arenes” Org. Lett. 2015, 17, 4312-4315. (DOI: 10.1021/acs.orglett.5b02129)


Deng, Y.; Jing, C.; Doyle, M.P. “Dinitrogen Extrusion from Enoldiazo Compounds under Thermal Conditions: Synthesis of Donor-Acceptor Cyclopropenes” Chem. Commun. 2015, 51, 12924-12927. (DOI: 10.1039/C5CC05006E)


Sha, Q.; Arman, H.; Doyle, M.P. “Three-Component Cascade Reactions with 2,3-Diketoesters: A Novel Metal-Free Synthesis of 5-Vinyl-pyrrole and 4-Hydroxy-indole Derivatives” Org. Lett.2015, 17, 3876–3879. (DOI: 10.1021/acs.orglett.5b01855)


Cheng, Q.-Q.; Qian, Y.; Zavalij, P.Y.; Doyle, M.P. “Lewis Acid/Rhodium-Catalyzed Formal [3+3]-Cycloaddition of Enoldiazoacetates with Donor–Acceptor Cyclopropanes” Org. Lett. 2015, 17, 3568-3571. (DOI: 10.1021/acs.orglett.5b01674)


Xu, X.; Wang, X.; Zavalij, P.Y.; and Doyle, M.P. “Straightforward Access to the [3.2.2]Nonatriene Structural Framework via Intramolecular Cyclopropenation/Buchner Reaction/Cope Rearrangement Cascade” Org. Lett. 2015, 17, 790-793. (DOI: 10.1021/ol503498n)


Xu, X.; Deng, Y.; Yim, D.N.; Zavalij, P.Y.; Doyle, M.P. “Enantioselective cis-β-Lactam Synthesis by Intramolecular C-H Functionalization from Enoldiazoacetamides and Derivative Donor-Acceptor Cyclopropenes” Chem. Sci.2015, 6, 2196-2201.( DOI: 10.1039/C4SC03991B)


Xu, X.; Doyle, M.P. “Divergent pathways of β,γ-unsaturated α-diazocarbonyl compounds catalyzed by dirhodium and Lewis acids catalysts separately or in combination” Chinese Chem. Lett. 2015, 26, 227-232. (DOI:10.1016/j.cclet.2014.12.014)


Liu,Y.; Deng, Y.; Liu, R.; Doyle, M.P. “An Efficient Route to Highly Enantioenriched Tetrahydroazulenes and β-Tetralones by Desymmetrization Reactions of δ,δ-Diaryldiazoacetoacetates” Chem. Commun. 2015, 51, 565-568. (DOI: 10.1039/c4cc08255a)


Angelone, D.; Draksharapu, A.; Browne, W.R.; Choudhuri, M.M.R.; Crutchley, R.J.; Xu, X.; Xu, X. Doyle, M.P. “Dinuclear Compounds Without a Metal-Metal Bond. Dirhodium(III,III) Carboxamidates” Inorg. Chim. Acta 2015, 424, 235-240. (DOI: 10.1016/j.ica.2014.09.006)


Truong, P.M.; Mandler, M.D.; Doyle, M.P. “The Chemistry of Vicinal Tricarbonyls: An Expedient Route to Fully-Substituted 3-Aminopyrroles” Tetrahedron Lett. 2015, 56, 3042-3045. (DOI: 10.1016/j.tetlet.2014.10.139)


Xu, X.; Wang, X.; Liu, Y.; Doyle, M.P. “Enantioselective Carbonyl-ene Reactions Catalyzed by Chiral Cationic Dirhodium(II,III) Carboxamidates” J. Org. Chem. 2014, 79, 12185-12190. (DOI: 10.1021/jo5013674)


Wilson, Z.S.; McGuire, S.Y.; Limbach, P.A.; Doyle, M.P.; Marzilli, L.G.; Warner, I.M. “Diversifying Science, Technology, Engineering, and Mathematics (STEM) – An empirical inquiry into successful approaches in chemistry” J. Chem. Educ. 2014, 91, 1860-1866. (DOI: 10.1021/ed400702v)


Ratnikov, M.O.; Doyle, M.P. “Dirhodium caprolactamate and tert-butyl hydroperoxide — a universal system for selective oxidations” Mendeleev Commun. 2014, 24, 187-252. (Focus article) (DOI: 10.1016/j.mencom.2014.06)


Liu, X.; Liu, X.; Shanahan, C.S.; Xu, X.; Doyle, M.P. “A Survey of Enoldiazo Nucleophilicity in Selective C-C Bond Forming Reactions for the Synthesis of Natural Product-Like Frameworks” Org. & Biomol. Chem. 2014, 12, 5227-5234. (DOI: 10.1039/C4OB00709C)


Truong, P.M.; Zavalij, P.Y.;Doyle, M.P. “Highly Enantioselective Carbonyl-Ene Reactions of 2,3-Diketoesters; Efficient and Atom-Economical Process to Functionalized Chiral α-Hydroxy-β-ketoesters” Angew. Chem. Int. Ed. 2014, 53, 6468–6472. (DOI: 10.1002/anie.201402233)


Xu, X.; Doyle, M.P. “The [3+3]-Cycloaddition Alternative for Heterocycle Syntheses: Catalytically Generated Metalloenolcarbenes as Dipolar Adducts” Acc. Chem. Res. 2014, 47, 1396-1405. (DOI: 10.1021/ar5000055)


Xu, X.; Leszczynski, J.S.; Mason, S.M.; Zavalij, P.Y.; Doyle, M.P. “Expedient Access to Substituted 3-Amino-2-cyclopentenones By Dirhodium-catalyzed [3+2]-Annulation of Silylated Ketene Imines and Enoldiazoacetates” Chem. Commun. 2014, 50, 2462-2464. (DOI:10.1039/C3CC48993K)


Mandler, M.D.; Truong, P.M.; Zavalij, P.Y.; Doyle, M.P. “Catalytic Conversion of Diazocarbonyl Compounds to Imines: Applications to the Synthesis of Tetrahydropyrimidines and β-Lactams” Org. Lett. 2014, 16, 740-743. (DOI: 10.1021/ol403427s)


Truong, P.M.; Mandler, M.D.; Shanahan, C.S.; Doyle, M.P. “Lewis Acid Catalyzed Diastereoselective 1,3-Dipolar Cycloaddition Between Diazoacetacetate Enones and Azomethine Ylides” Heterocycles 2014, 88, 1039-1049. (DOI: 10.3987/COM-13-S(S)63)


Xu, X.; Doyle, M.P. “Recent Developments in the Synthetic Uses of Silyl-protected Enoldiazoacetates for Heterocyclic Syntheses” Austral. J. Chem.2014, 67, 365-373. (


Shabashov, D.; Doyle, M.P. “Rhodium Acetate-Catalyzed Aerobic Mukaiyama Epoxidation of Alkenes” Tetrahedron 2013, 69, 10009-10013. (DOI: 10.1016/j.tet.20)


Xu, X.; Zavalij, P.Y.; Doyle, M.P. “Highly Enantioselective Dearomatizing Formal [3+3]-Cycloaddition Reactions of N-Acyliminopyridinium Ylides with Electrophilic Enolcarbene Intermediates” Angew. Chem. Int. Ed. 2013, 52, 12664-12668. (


Xu, X.; Zavalij, P.J.; Doyle, M.P. “A Donor-Acceptor Cyclopropene as a Dipole Source for a Silver(I) Catalyzed Asymmetric Catalytic [3+3]-Cycloaddition with Nitrones” Chem. Commun. 2013, 49, 10287-10289. (DOI: 10.1039/c3cc46415f)


Xu, X.; Zavalij, P.Y.; Doyle, M.P. “Catalytic Asymmetric Syntheses of Quinolizidines by Dirhodium-catalyzed Dearomatization of Isoquinolinium/Pyridinium Methylides – The Role of Catalyst and Carbene Source” J. Am. Chem. Soc. 2013, 135, 12439-12447. (DOI: 10.1021/ja406482q)


Qian, Y.; Shanahan, C.S.; Doyle, M.P. “Templated Carbene Metathesis Reactions from the Modular Assembly of Enoldiazo Compounds and Propargyl Acetates” Eur. J. Org. Chem. 2013, 6032-6037. (DOI: 10.1002/ejoc.201301000)


Shanahan, C.S.; Truong, P.; Mason, S.M.; Leszczynski, J.S.; Doyle, M.P. “Diazoacetoacetate Enones for the Synthesis of Diverse Natural Product-like Scaffolds” Org. Lett. 2013, 15, 3642-3645. (DOI: 10.1021/ol4015199)


Truong, P.M.; Mandler, M.D.; Zavalij, P.Y.; Doyle, M.P. “Tetrahydroquinolines and Benzazepines through Catalytic Diastereoselective Formal [4+2]-Cycloaddition Reactions Between Donor-Acceptor Cyclopropenes and Imines” Org. Lett. 2013, 15, 3278-3281. (DOI: 10.1021/ol401308d)


Ratnikov, M.O.; Xu, X.; Doyle, M.P. “Simple and Sustainable Iron-Catalyzed Aerobic C-H Functionalization of N,N-Dialkylanilines” J. Am. Chem. Soc. 2013, 135, 9475-9479. (DOI: 10.1021/ja402479r)


Qian, Y.; Zavalij, P.Y.; Hu, W.; Doyle, M.P. “Bicyclic Pyrazolidinone Derivatives from Diastereoselective Catalytic [3+3]-Cycloaddition Reactions of Enoldiazoacetates with Azomethine Imines” Org. Lett. 2013, 15, 1564-1567. (DOI: 10.1021/ol400339c)


Xu, X.; Xu, X.; Zavalij, P.Y.; Doyle, M.P. “Dirhodium(II)-Catalyzed Formal [3+2+1]-Annulation of Azomethine Imines with Two Molecules of a Diazo Ketone” Chem. Commun. 2013, 49, 2762-2764. (DOI:10.1039/c3cc41119b)


Xu, X.; Zavalij, P.Y.; Hu, W.; Doyle, M.P. “Vinylogous Reactivity of Enoldiazoacetates with Donor-Acceptor Substituted Hydrazones. Synthesis of Highly Substituted Pyrazole Derivatives” J. Org. Chem. 2013, 78, 1583-1588. (DOI: 10.1021/jo302696y)


Xu, X.; Qian, Y.; Zavalij, P.Y.; Doyle, M.P. “Highly Selective Catalyst-Dependent Competitive 1,2-C→C, -O→C and -N→C Migrations from β-Methylene-β-silyloxy-β-amido-α-Diazoacetates” J. Am. Chem. Soc. 2013, 135, 1244-1247. (DOI: 10.1021/ja311392m)


Ratnikov, M.O.; Doyle, M.P. “Mechanistic Investigation of Oxidative Mannich Reaction with tert-Butyl Hydroperoxide. The Role of Transition Metal Salt” J. Am. Chem. Soc. 2013, 135, 1549-1557. (DOI: 10.1021/ja3113559)


Ratnikov, M.O.; Farkas, L.E.; Doyle, M.P. “Tandem Sequence of Phenol Oxidation and Intramolecular Addition as a Method in Building Heterocycles” J. Org. Chem. 2012, 77, 10294-10303.


Xu, X.; Zavalij, P.Y.; Hu, W.; Doyle, M.P. “Efficient Synthesis of Oxazoles by Dirhodium(II)-Catalyzed Reactions of Styryl Diazoacetate with Oximes” Chem. Commun. 2012, 48, 11522 – 11524.


Xu, X.; Zavalij, P.Y.; Doyle, M.P. “Synthesis of Tetrahydropyridazines by a Metal-carbene Directed Highly Enantioselective Vinylogous N-H Insertion/Lewis Acid Catalyzed Diastereoselective Mannich Addition” Angew. Chem. Int. Ed. 2012, 51, 9829-9833; Angew. Chem. 2012, 124, 9967-9971


Qiu, H.; Li, M.; Jiang, L.-Q.; Lv, F.-P.; Zan, L.; Zhai, C.-W.; Doyle, M.P.; Hu, W.-H. “Highly Enantioselective Trapping of Zwitterionic Intermediates by Imines” Nature Chemistry 2012, 4, 733-738.


Doyle, M.P.; Liu, Y. “Michael Addition/Pericyclization/Rearrangement – A Multicomponent Strategy for the Synthesis of Substituted Resorcinols” Org. Biomol. Chem. 2012, 10, 6388-6394.


Xu, X.; Shabashov, D.; Zavalij, P.Y.; Doyle, M.P. “Substrate-Dependent Divergent Outcomes from Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides: Azabicyclo[3.1.0]hexanes or 5-Arylaminofuran-2(3H)-ones” J. Org. Chem. 2012, 74, 5313–5317.


Qian, Y.; Xu, X.; Wang, X.; Zavalij, P.J.; Hu, W.; Doyle, M.P. “Rhodium(II) and Copper(II) Catalyzed Reactions of Enoldiazoacetates with Nitrones. Metal Carbene versus Lewis Acid Directed Pathways” Angew. Chem. Int. Ed. 2012, 51, 5900-5903; Angew. Chem. 2012, 124, 6002–6005.


Trong, P.; Shanahan, C.S.; Doyle, M.P. “Divergent Stereocontrol of Acid Catalyzed Intramolecular Aldol Reactions of 2,3,7-Triketoesters: Synthesis of Highly Functionalized Cyclopentanones” Org. Lett. 2012, 14, 3608-3611.


Wang, X.; Abrahams, Q.M.; Zavalij, P.Y.; Doyle, M.P. “Highly Regio- and Stereoselective Dirhodium Vinylcarbene-induced Nitrone Cycloaddition with Subsequent Cascade Carbenoid Aromatic Cycloaddition/N-O Cleavage and Rearrangement” Angew. Chem. Int. Ed. 2012, 51, 5907-5910; Angew. Chem. 2012, 124, 6009–6012.


Jaber, D.M.; Burgin, R.N.; Helper, M.; Zavalij, P.Y.; Doyle, M.P. “Competitive [2,3]- and [1,2]-Oxonium Ylide Rearrangements. Concerted or Stepwise?” Org. Lett. 2012, 14, 1676-1679.


Marbach-Ad, G.; Schaefer, K.L.; Kumi, B.C.; Friedman, L.A.; Thompson, K.V.; Doyle, M.P. “Development and Evaluation of a Prep Course for Chemistry Graduate Teaching Assistants at a Research University” J. Chem. Educ. 2012, 89, 865–872.


Xu, X.; Shabashov, D.; Zavalij, D.; Doyle, M.P. “Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3H)-one-4-carboxylates” Org. Lett. 2012, 14, 800-803.


Ratnikov, M.O.; Goldmann, P.L.; McLaughlin, E.C.; Doyle. M.P. (Checked by Zhang, K.; Majumder, S.; Brummond, K.) “Allylic Oxidation Catalyzed by Dirhodium(II) Tetrakis[ε-caprolactamate] of tert-Butyldimethylsilyl-protected trans-Dehydroandrosterone” Org. Synth2012, 89, 19-33.


Xu, X.; Ratnikov, M.O.; Zavalij, P.Y.; Doyle, M.P. “Multifunctionalized 3-Hydroxypyrroles in a Three-Step, One-Pot Cascade Process from Methyl 3-TBSO-2-diazo-3-butenoate and Nitrones” Org. Lett. 2011, 13, 6122-6125.


Wang, X.; Xu, X.; Zavalij, P.Y.; Doyle, M.P. “Asymmetric Formal [3+3] Cycloaddition Reactions of Nitrones with Electrophilic Vinylcarbene Intermediates” J. Am. Chem. Soc. 2011, 133, 16402-16405.


Xu, X.; Hu, W.-H.; Doyle, M.P. “Divergent Outcomes from Catalysis by Dirhodium and Copper Separately or in Combination” Angew. Chem. Int. Ed. 2011, 50, 11152-11155; Angew. Chem. 2011, 123, 11348-11351.


Doyle, M.P. “Silver Catalyzed Carbene Functionalization of Methane in Supercritical Carbon Dioxide” ChemCatChem 2011, 3,1681-1682.


Xu, X.; Doyle, M.P. “Enantiomer Recognition of Amides by Chiral Dirhodium(II) Carboxamidates” Inorg. Chem. 2011, 50, 7610-7617.


Doyle, M.P.; Shabashov, D.; Zhou, L.; Zavalij, P.Y.; Welch, C.; Pirzada, Z. “Does an Axial Propeller Shape on a Dirhodium(III,III) Core Affect Equatorial Ligand Chirality?” Organometal. 2011, 30, 3619-3627.


Jaber, D.M.; Burgin, R.N.; Hepler, M.; Zavalij, P.; Doyle, M.P. “Control of Selectivity in the Generation and Reactions of Oxonium Ylides” Chem. Commun. 2011, 47, 7623-7625.


Wang, X.; Weigl, C.; Doyle, M.P. “Solvent Enhancement of Reaction Selectivity: A Unique Property of Cationic Chiral Dirhodium Carboxamidates” J. Am. Chem. Soc. 2011, 133, 9572-9579.


Xu, X.; Hu, W.-H.; Doyle, M.P. “Highly Enantioselective Catalytic Synthesis of Functionalized Chiral Diazoacetoacetates” Angew. Chem. Int. Ed.2011, 50, 6392-6395; Angew. Chem. 2011, 123, 6516-6519.


Ratnikov, M.O.; Farkas, L.E.; McLaughlin, E.C.; Chiou, G.; Choi, H.; El-Khalafy, S.H.; Doyle, M.P. “Dirhodium-Catalyzed Phenol and Aniline Oxidations with T-HYDRO. Substrate Scope and Mechanism of Oxidation” J. Org. Chem. 2011, 73, 2585-2593.


Doyle, M.P.; Ratnikov, M.; Liu, Y. “Intramolecular catalytic asymmetric carbon-hydrogen insertion reactions. Synthetic advantages in comparison with alternative approaches” Org. Biomol. Chem. 2011, 9, 4007-4016. Perspective. (Journal Cover)


Truong, P.; Xu, X.; Doyle, M.P. “An Efficient Methodology to Substituted Furans via Oxidation of Functionalized α-Diazo-β-ketoacetates” Tetrahedron Lett. 2011, 52, 2093-2096. (special issue honoring Harry Wasserman)


Bohorquez, A.R.; Kouznetsov, V.V.; Doyle, M.P. “Cu(OTf)2-Catalyzed Three-Component Imino Diels-Alder Reaction Using Propenylbenzenes: Synthesis of 2,4-Diaryl Tetrahydroquinoline Derivatives” Lett. Org. Chem. 2011, 8, 5-11.


Liu, Y.; Bakshi, K.; Zavalij, P.; Doyle, M.P. “Pericyclic Reaction of a Zwiterionic Salt of an Enedione-diazoester. A Novel Strategy for the Synthesis of Highly Functionalized Resorcinols” Org. Lett. 2010, 12, 4303-4307.


Zhang, Y.; Doyle, M.P. “Chemoselectivity in Dirhodium(II) Catalyzed Reactions of Diazoacetoacetates Prepared from α,β-Unsaturated Ketones” ARKOVIC 2010, viii, 10-16. (special issue in honor of Bruce and Cyndie Maryanoff)


Doyle, M.P. “The Evolving Nature of Chemical Education: Challenges and Opportunities” Future Med. Chem. 2010, 2(2), 247-249.


Doyle, M.P.; Duffy, R.; Ratnikov, M.; Zhou, L. “Catalytic Carbene Insertion into C-H Bonds” Chem. Rev.2010, 110, 704-724.


Zhou, L; Doyle, M.P. “Stereoselective Synthesis of Highly Functionalized α-Diazo-β-ketoalkanoates via Catalytic One-Pot Mukayama-Aldol Reactions” Org. Lett. 2010, 12, 796-799.

285.Xie, J.-H.; Doyle, M.P. “On the Origin of the Conformationally Non-Interconvertable Isomers of Bisphenyldirhodium(III) Caprolactamate” J. Mex. Chem. Soc2009, 53, 143-146. (special issue dedicated to the memory of Ernest Eliel)
284.Zhou, L.; Doyle, M.P. “Lewis Acid Catalyzed Indole Synthesis via Intramolecular Nucleophilic Attack of Phenyldiazoacetates to Iminium Ions” J. Org. Chem. 2009, 74, 9222-9224.
283.Wang, X.; Li, Z.; Doyle, M.P. “Barriers to Enantiocontrol in Lewis Acid Catalyzed Hetero-Diels-Alder Reactions” Chem. Commun. 2009, 5612-5614.
282.Doyle, M.P.; Xie, J.-H.; Zhou, L.; Sun, Y.; Liu, Y.; Sun, H. “Conformational Isomers of Extraordinary Stability: Carboxamidate-Bridged Dimetalloorganic Compounds,” Chem. Commun. 2009, 3005-3007.
281.Xie, J.-H.; Zhou, L.; Lubek, C.; Doyle, M.P. “Hetero-bis(σ-aryl)dirhodium(III) Caprolactamates. Electronic Communication Between Aryl Groups Through Dihodium(III)” Dalton Trans. 2009, 2871-2877.
280.Doyle, M.P. “Exceptional Selectivity in Cyclopropanation Reactions Catalyzed by Chiral Cobalt(II) Porphyrins” Angew. Chem. Int. Ed. 2009, 48, 850-852.
279.McLaughlin, E.C.; Choi, H.; Wang, K.; Chiou, G.; Doyle, M.P. “Allylic Oxidations Catalyzed by Dirhodium Caprolactamate via Aqueous tert-Butyl Hydroperoxide: The Role of the tert-Butylperoxy Radical” J. Org. Chem. 2009, 74, 730-738.
278.Gladwin, M.T.; Grubina, R.; Doyle, M.P. “The New Chemical Biology of Nitrite Reactions with Hemoglobin: R-state Catalysis, Oxidative Denitrosylation and Nitrite Reductase/Anhydrase” Acc. Chem. Res. 2009, 42, 157-167.
277.Wolf, J.; Poli, R.; Xie, J.-H.; Nichols, J.; Xi, B.; Zavalij, P.; Doyle, M.P. “Removal of Metal-Metal Bonding in a Dimetallic Paddlewheel Complex – Molecular and Electronic Structure of Bis(phenyl) Dirhodium(III) Carboxamidate Compounds” Organometal2008, 27, 5836-5845.
276.McLaughlin, E.C.; Doyle, M.P. “Propargylic Oxidations Catalyzed by Dirhodium Caprolactamate in Water: Efficient Access to α,β-Acetylenic Ketones” J. Org. Chem. 2008, 73, 4317-4319.
275.Xie, J.-H.; Nichols, J.M.; Lubek, C.; Doyle, M.P. “Synthesis of Bis(α-aryl)dirhodium(III) Caprolactamates by Oxidative Arylation With Arylboronic Acids” Chem. Commun. 2008, 2671-2673.
274.Liu, Y.; Zhang, Y.; Jee, N.; Doyle, M.P. “Construction of Highly Functionalized Diazoacetoacetates via Catalytic Mukaiyama-Michael Reactions” Org. Lett. 2008, 10, 1605-1608.
273.Nichols, J.M.; Liu, Y.; Zavalij, P.; Isaacs, L.; Doyle, M.P. “Diphenylglycoluril as a Novel Ligand Architecture for Dirhodium(II) Carboxamidates” Inorg. Chim. Acta 2008, 361, 3309-3314. (special issue honoring R. Angelici)
272.Wang, Y.; Wolf, J.; Zavalij, P.; Doyle, M.P. “Cationic Chiral Dirhodium Carboxamidates are Activated for Lewis Acid Catalysis” Angew. Chem. Int. Ed. 2008, 47, 1439-1442; Angew. Chem. 2008, 120, 1461-1464.
271.Choi, H.; Doyle, M.P. “Optimal TBHP Allylic Oxidation of Δ5-Steroids Catalyzed by Dirhodium Caprolactamate” Org. Lett. 2007, 9, 5349-5352.
270.Nichols, J.M.; Wolf, J.; Zavalij, P.; Varughese, B.; Doyle, M.P. “Bis(phenyl)dirhodium(III) Caprolactamate: A Dinuclear Paddlewheel Complex With No Metal-Metal Bond” J. Am. Chem. Soc. 2007, 129, 3504-3505.
269.Choi, H.; Doyle, M.P. “Oxidation of Secondary Amines Catalyzed by Dirhodium Caprolactamate” Chem. Commun. 2007, 745-747.
268.Doyle, M.P. “Perspective on Dirhodium Carboxamidates as Catalysts” J. Org. Chem. 2006, 71, 9253-9260. Invited.
267.Bykowski, D.; Wu, K.-H.; Doyle, M.P. “Vinyldiazolactone as a Vinylcarbene Precursor: Highly Selective C-H Insertion and Cyclopropanation Reactions” J. Am. Chem. Soc. 2006, 128, 16038-16039.
266.Doyle, M.P.; Weathers, Jr., T.M.; Wang, Y. “Stereoselectivity in the Cyclopropenation of a Carbon-Carbon Triple Bond Linked to the Reactant Diazoacetate Through a Chiral Linker” Adv. Synth. & Catal. 2006, 348, 2403-2409. (guest editor of issue)
265.Weathers, Jr., T.M.; Wang, Y.; Doyle, M.P. “Polyether Macrocycles from Intramolecular Cyclopropanation and Ylide Formation. Effect of Catalyst and Coordination” J. Org. Chem. 2006, 71, 8183-8189.
264.Catino, A.J.; Nichols, J.M.; Nettles, B.J.; Doyle, M.P. “The Oxidative Mannich Reaction Catalyzed by Dirhodium Caprolactamate” J. Am. Chem. Soc.2006, 128, 5648-5649.
263.Welch, C.J.; Tu, Q.; Wang, T.; Raab,C.; Wang, P.; Jia, X.; Bu, X.; Bykowski, D.; Hohenstaufen, B.; Doyle, M.P. “Observations of Rh-Containing Reaction Intermediates Using HPLC with ICP-MS and ESI-MS Detection” Adv. Synth. & Catal. 2006, 348, 821-825.
262.Kundu, K.; Doyle, M.P. “Constructing Chiral Diazoacetoacetates by Enantioselective Catalytic Mukaiyama Aldol Reactions” Tetrahedron: Asymmetry2006, 17, 574-577. (special issue entitled “Frontiers in Asymmetric Catalysis”)
261.Tu, Q.; Wang, T.; Welch, C.J.; Wang, P.; Jia, X.; Raab, C.; Bu, X.; Bykowski, D.; Hohenstaufen, B.; Doyle, M.P. “Identification and Characterization of Isomeric Intermediates in a Catalyst Formation Reaction by Means of Speciation Analysis Using HPLC-ICPMS and HPLC-ESI-MS” Anal. Chem. 2006, 78, 1282-1289.
260.Weathers Jr., T.M.; Doyle, M.P.; Carducci, M.D. “Substrate versus Catalyst Control of Stereoselectivity in the Cyclopropanation of a Carbon-Carbon Double Bond Linked to the Reactant Diazoacetate Through a Chiral Linker” Adv. Synth. & Catal. 2006, 348, 449-455.
259.Catino, A.J.; Nichols, J.M.; Choi, H.; Gottipamula, S.; Doyle, M.P. “Benzylic Oxidation Catalyzed by Mixed-Valent Dirhodium(II,III) Caprolactamate” Org. Lett. 2005, 7, 5167-5170.
258.Doyle, M.P.; Kundu, K.; Russell, A.E. “Catalytic Addition Methods for the Synthesis of Functionalized Diazoacetoacetates and Application to the Construction of Highly Substituted Cyclobutanones” Org. Lett. 2005, 7, 5171-5174.
257.Doyle, M.P.; Wang, Y.; Ghorbani, P.; Bappert, E. “Amplification of Asymmetric Induction in Sequential Reactions of Bis-diazoacetates Catalyzed by Chiral Dirhodium(II) Carboxamidates” Org. Lett. 2005, 7, 5035-5038.
256.Doyle, M.P.; Morgan, J.P.; Colyer, J.T. “Stereoselectivity in Metal Carbene and Lewis Acid-Catalyzed Reactions from Diastereomeric Dirhodium(II) Carboxamidates: Menthyl N-Acetyl-2-oxoimidazolidine-4(S)-carboxylates” J. Organometal. Chem. 2005, 690, 5525-5532.
255.Morgan, J.P.; Kundu, K.; Doyle, M.P. “A Readily Prepared Neutral Heterobimetallic Titanium(IV)-Rhodium(I) Catalyst for Intramolecular Hydroacylation” Chem. Commun. 2005, 3307-3309.
254.Catino, A.J.; Nichols, J.M.; Forslund, R.E.; Doyle, M.P. “Efficient Aziridination of Olefins Catalyzed by Mixed Valent Dirhodium(II,III) Caprolactamate” Org. Lett2005, 7, 2787-2790.
253.Doyle, M.P.; Morgan, J.P.; Fettinger, J.; Colyer, J.T.; Timmons, D.J.; Carducci, M. “Matched/Mismatched’ Diastereomeric Dirhodium(II) Carboxamidate Catalyst Pairs. Structure/Selectivity Correlations in Diazo Decomposition and Hetero-Diels-Alder Reactions” J. Org. Chem. 2005, 70, 5291-5301.
252.Forslund, R.E.; Cain, J.; Doyle, M.P. “Chiral Dirhodium(II) Carboxamidate Catalyzed [2+2] Cycloaddition of TMS-Ketene and Ethyl Glyoxylate” Adv. Synth. & Catal. 2005, 347, 87-92.
251.Yan, M.; Jacobsen, N.; Hu, W.; Gronenberg, L.; Doyle, M.P.; Colyer, J.T.; Bykowski, D. “Stereoselective Synthesis of Bicyclic Pyrrolidines via a Rhodium Catalyzed Cascade Process” Angew. Chem. Int. Ed. 2004, 43, 6713-6716; Angew. Chem. 2004, 116, 6881-6884.
250.Catino, A.J.; Forslund, R.E.; Doyle, M.P. “Dirhodium(II) Caprolacatamate: An Exceptional Catalyst for Allylic Oxidation” J. Am. Chem. Soc. 2004, 126, 13622-13623. Highlighted in Science, volume 306, issue 22, October 2004.
249.Valenzuela, M.; Doyle, M.P.; Hedberg, C.; Hu, W.; Holmstrom, A. “Influence of the Diene in the Hetero-Diels-Alder Reaction Catalyzed by Dirhodium(II) Carboxamidates” Synlett 2004 (invited, special issue on Asymmetric Lewis Acid Catalysis, H. Yamamoto, Ed.), 2425-2428.
248.Russell, A.E.; Brekan, J.; Gronenberg, L.; Doyle, M.P. “Divergence of Carbonyl Ylide Reactions as a Function of Diazocarbonyl Compound and Aldehyde Substituent – Dioxolanes, Dioxolenes, and Epoxides” J. Org. Chem. 2004, 69, 5269-5274.
247.Lu, C.-D.; Chen, Z.-Y.; Liu, H.; Hu, W.-H.; Mi, A.-Q.; Doyle, M.P. “A Facile Three-Component One-Pot Synthesis of Structurally Constrained Tetrahydrofurans That are t-RNA Synthetase Inhibitor Analogues” J. Org. Chem. 2004, 69, 4856-4859.
246.Doyle, M.P.; Valenzuela, M.; Huang, P. “Asymmetric Hetero-Diels-Alder Reactions Catalyzed by Dirhodium(II) Carboxamidates” Proc. Nat’l. Acad. Sci. 2004, 101, 5391-5395.
245.Wang, Y.; Zhu, Y.; Chen, Z.; Mi, A.; Hu, W.; Doyle, M.P. “A Novel Three-Component Reaction Catalyzed by Dirhodium(II) Acetate: Decomposition of Phenyldiazoacetate with Arylamine and Imine for Highly Diastereoselective Synthesis of 1,2-Diamines” Org. Lett. 2003, 5, 3923-3926.
244.Doyle, M.P.; Colyer, J.T. “Synthesis of Dirhodium(II) Tetrakis[methyl 1-(3-Phenylpropanoyl)-2oxaimidazolidine-4(S)-carboxylate], 
Rh2(4S-MPPIM)4” Tetrahedron Asymmetry 2003, 14, 3601-3604
243.Doyle, M.P.; Yan, M.; Hu, W.; Gronenberg, L. S. “Highly Selective Catalyst-Directed Pathways to Dihydropyrroles from Vinyldiazoacetates and Imines” J. Am. Chem. Soc. 2003, 125, 4692-4693.
242.Doyle, M.P.; Hu, W. “Enantioselectivity for Catalytic Cyclopropanation with Diazomalonates” ARKIVOC 2003, part (vii), 125, 4692-4693. (commemorative issue in honor of Professor M. A. McKervey on the occasion of his retirement from Queen’s University)
241.Doyle, M.P.; Gau, H.-M.; Blossey, E.C.; Yan, M. “Catalysts with Mixed Ligands on Immobilized Supports. Electronic and Steric Advantages” Org. Lett. 2003, 5, 561-563.
240.Doyle, M.P.; Catino, A.J. “A Short Stereoselective Synthesis of (+)- and (-)-2-Oxabicyclo[3.3.0]oct-6-en-3-one by Intramolecular Carbon-Hydrogen Insertion Catalyzed by Chiral Dirhodium(II) Carboxamidates” Tetrahedron: Asymmetry 2003, 14, 925-928. (invited, special edition “Catalytic Asymmetric Carbene Transfer Reactions” Davies, H. M. L. editor-in-charge)
239.Doyle, M.P.; Hu, W.; Weathers, Jr., T.M. “Comparative Enantiocontrol with Allyl Phenyldiazoacetates in Asymmetric Catalytic Intramolecular Cyclopropanation” Chirality 2003, 15, 369-373. (invited, special issue honoring K. Barry Sharpless)
238.Doyle, M.P.; Hu, W.; Wee, A.G. H.; Wang, Z.; Duncan, S.C. “Influences of Catalyst Configuration and Catalyst Loading on Selectivities in Reactions of Diazoacetamides. Barrier to Equilibrium Between Diastereomeric Conformations” Org. Lett. 2003, 5, 407-410. Addition/Correction: Org. Lett.2003, 5, 2371
237.Doyle, M.P.; Yang, M. “Attempted Synthesis of Casbene by Intramolecular Cyclopropanation” ARKIVOC 2002, Part (viii), 180-185. (commemorative issue in Honor of Professor Albert Padwa on his 65th anniversary)
236.Doyle, M.P. “Academic Excellence – The Role of Research” J. Chem. Educ2002, 79, 1038-1045.
235.Doyle, M.P.; Colyer, J.T. “Steric Balance within Chiral Dirhodium(II) Carboxamidate Catalysts Enhances Stereoselectivity” J. Molecular Catalysis A: Chemical 2003, 196, 93-100.
234.Doyle, M.P.; Yang, M. “Chiral Catalyst Enhancement of Diastereocontrol for O–H Insertion Reactions of Styryl- and Phenyldiazoacetate Esters of Pantolactone” Tetrahedron Lett. 2002, 43, 5929-5931.
233.Doyle, M.P.; Timmons, D.J.; Tumonis, J.S.; Gau, H.-M.; Blossey, E.C. “Preparation and Catalytic Properties of Immobilized Chiral Dirhodium(II) Carboxamidates” Organometallics 2002, 21, 1747-1749.
232.W. Hu; Timmons, D.J.; Doyle, M.P. “In Search of High Stereocontrol for the Construction of cis-Disubstituted Cyclopropane Compounds. Total Synthesis of a Cyclopropane-Configured Urea-PETT Analog That is a HIV-1 Reverse Transcriptase Inhibitor” Org. Lett. 2002, 4, 901-904.
231.Doyle, M.P.; Hu, W.; Valenzuela, M.V. “Total Synthesis of (S)-(+)-Imperanene. Effective use of Regio- and Enantioselective Intramolecular Carbon-Hydrogen Insertion Reactions Catalyzed by Chiral Dirhodium(II) Carboxamidates” J. Org. Chem. 2002, 67, 2954-2959.
230.Doyle, M.P.; Hu, W. “Enantioselective Carbon-Hydrogen Insertion is an Effective and Efficient Methodology for the Synthesis of (R)-(-)-Baclofen” Chirality 2002, 14, 169-172. (special issue honoring E. Eliel)
229.Doyle, M.P.; Phillips, I.M.; Yan, M.; Timmons, D.J. “Highly Selective Synthesis of a 2-Deoxyxylolactam via Enantioselective Carbon-Hydrogen Insertion Reactions Using Chiral Dirhodium(II) Carboxamidates” Adv. Synth. & Cat. 2002, 344, 91-95.
228.Doyle, M.P.; Yan, M. “Effective and Highly Stereoselective Coupling with Vinyldiazomethanes to Form Symmetrical Trienes” J. Org. Chem. 2002, 67, 602-604.
227.Doyle, M.P.; Timmons, D.J.; Arndt, M.M.R.; Duursma, A.; Colyer, J.T.; Brunner, H. “First Attempts at Differential Diastereoselection in Catalytic Reactions of Dirhodium(II) Tetrakis-[Methyl N-(chiral attachment)-2-oxamidazolidine-4(S)-carboxylates] with Diazoacetates” Russ. Chem. Bull.2001, 51, 2156-2161. (special issue honoring O. Nefedov)
226.Doyle, M.P., Hu, W.; Timmons, D.J. “Highly Stereoselective Syntheses of Five- and Seven-Membered Ring Heterocycles from Ylides Generated by Catalytic Reactions of Styryldiazoacetates with Aldehydes and Imines” Org. Lett. 2001, 3, 3741-3744.
225.Doyle, M.P.; Davies, S.B.; May, E.J. “High Selectivity from Configurational Match/Mismatch in Carbon-Hydrogen Insertion Reactions of Steroidal Diazoacetates Catalyzed by Chiral Dirhodium(II) Carboxamidates” J. Org. Chem. 2001, 66, 8112-8119.
224.Doyle, M.P.; W. Hu “Macrocycle Formation from Catalytic Metal Carbene Transformations,” Synlett 2001, 1364-1370.
223.Doyle, M.P.; May, E.J. “Enantioselective β-Lactone Formation from Phenyldiazoacetates via Catalytic Intramolecular Carbon-Hydrogen Insertion” Synlett 2001, 967-969. (special issue honoring R. Noyori)
222.Doyle, M.P., Phillips, I.M.; Hu, W. “A New Class of Chiral Lewis Acid Catalysts for Highly Enantioselective Hetero-Diels-Alder Reactions: Exceptionally High Turnover Numbers from Dirhodium(II) Carboxamidates” J. Am. Chem. Soc. 2001, 123, 5366-5367.
221.Doyle, M.P.; Hu, W. “A New Enantioselective Synthesis of Milnacipran and an Analog by Catalytic Asymmetric Cyclopropanation” Adv. Synth. & Cat. 2001, 343, 299-302.
220.Doyle, M.P.; Phillips, I.M. “Cyclopropanation versus Carbon-Hydrogen Insertion. The Influences of Substrate and Catalyst on Selectivity” Tetrahedron Lett. 2001, 42, 3155-3158.
219.Doyle, M.P., Hu, W.; Timmons, D.J. “Epoxides and Aziridines from Diazoacetates via Ylide Intermediates” Org. Lett. 2001, 3, 933-935.
218.Doyle, M.P., Hu, W.; Phillips, I.M.; Moody, C.J.; Pepper, A.G. “Reactivity Enhancement for Chiral Dirhodium(II) Tetrakis(carboxamidates)” Adv. Synth. & Cat. 2001, 343, 1, 112-117.
217.Timmons, D.J.; Doyle, M.P. “Catalyst Selection for Metal Carbene Transformations” J. Organometal. Chem. 2001, 617-618, 94-104. (invited review)
216.Doyle, M.P.; Hu, W. “Enantiocontrol in Macrocycle Formation from Catalytic Metal Carbene Transformations” Chinese J. of Chem. 2001, 19, 22-29. (invited review)
215.Doyle, M.P., Hu, W. “Selectivity in Reactions of Allyl Diazoacetates as a Function of Catalyst and Ring Size from γ-Lactones to Macrocyclic Lactones” J. Org. Chem. 2000, 65, 8839-8847 (Dec. 29, 2000 cover art)
214.Doyle, M.P.; Hu, W. “Reactivities and Selectivities in Macrocyclic Addition Reactions with Diazoacetates using Copper(I) and Rhodium(II) Catalysts” Tetrahedron Lett. 2000, 41, 6265-6269.
213.Doyle, M.P.; Hu, W.; Phillips, I.M.; Wee, A.G.H. “A New Approach to Macrocyclization via Alkene Formation in Catalytic Diazo Decomposition. Synthesis of Patulolides A and B” Org. Lett. 2000, 2, 1777-1779.
212.Doyle, M.P., Hu, W.; Chapman, B.; Marnett, A.B.; Peterson, C.S.; Vitale, J.P.; Stanley, S.A. “Enantiocontrolled Macrocycle Formation by Catalytic Intramolecular Cyclopropanation” J. Am. Chem. Soc. 2000, 122, 5718-5728.
211.Doyle, M.P., Davies, S.B.; Hu, W. “Optimization of Enantiocontrol in cis-Selective Cyclopropanation Reactions Catalyzed by Dirhodium(II) Tetrakis[alkyl 2-oxaazetidine-4(S)-carboxylates]” J. Chem. Soc., Chem. Commun. 2000, 867-868.
210.Doyle, M.P.; Davies, S.B.; Hu, W. “Dirhodium(II) Tetrakis[methyl 2-oxaazetidine-4-carboxylate]: A Chiral Dirhodium(II) Carboxamidate of Exceptional Reactivity and Selectivity” Organic Lett. 2000, 2, 1145-1147.
209.Doyle, M.P., Tedrow, J.S.; Dyatkin, A.B.; Spaans, C.J.; Ene, D.G. “Enantioselective Synthesis of 2-Deoxyxylono-1,4-lactone and 2-Deoxyribono-1,4-lactone from 1,3-Dioxan-5-yl Diazoacetates” J. Org. Chem. 1999, 64, 8907-8915.
208.Doyle, M.P. “Control of Enantioselectivity in Catalytic Metal Carbene Reactions” Enantiomer 1999, 4, 621-632. (invited review)
207.Doyle, M.P., Chapman, B.J.; Hu, W.; Peterson, C.S. “Catalytic Intramolecular Addition of Metal Carbenes to Remote Furans” Org. Lett. 1999, 1, 1327-1329.
206.Doyle, M.P.; Ene, D.G.; Forbes, D.C.; Pillow, T.H. “Chemoselectivity and Enantiocontrol in Catalytic Intramolecular Metal Carbene Reactions of Diazoacetates Linked to Reactive Functional Groups by 1,8-Naphthalenedimethanol” J. Chem. Soc., Chem. Commun. 1999, 1691-1692.
205.Doyle, M.P. “Enantiocontrol in Catalytic Metal Carbene Reactions,” Russ. Chem. Bull. 1999, 48, 16-20. (invited review)
204.Doyle, M.P.; Ene, D.G.; Peterson, C.S.; Lynch, V. “Macrocyclic Cyclopropenes by Highly Enantioselective Intramolecular Addition of Metal Carbenes to Alkynes” Angew. Chem. Int. Ed. 1999, 38, 700-702; Angew. Chem.1999, 111, 722-724.
203.Doyle, M.P.; “New Catalysts and Methods for Highly Enantioselective Metal Carbene Reactions” Pure & Appl. Chem. 1998, 70, 1123.
202.Doyle, M.P.; Protopopova, M.N. “New Aspects of Catalytic Asymmetric Cyclopropanation” Tetrahedron (Tetrahedron Report number 457) 1998, 54, 7919-7946.
201.Doyle, M.P.; Forbes, D.C.; Vasbinder, M.M.; Peterson, C.S. “Enantiocontrol in the Generation and Diastereoselective Reactions of Oxonium Ylides Catalyzed by Chiral Dirhodium(II) Carboxamidates. Metal-Stabilized Ylides as Reaction Intermediates” J. Am. Chem. Soc. 1998, 120, 7653-7654.
200.Doyle, M.P.; Forbes, D.C.; Xavier, K.R. “Dirhodium(II) Catalyzed Carbonyl Ylide Generation. Stereoelectronic Control in Dioxolane Formation” Russ. Chem. Bull. 1998, 47, 932-935.
199.Forbes, D.C.; Ene, D.G.; Doyle, M.P. “Stereoselective Synthesis of Substituted 5-Hydroxy-1,3-dioxanes” Synthesis 1998, 879-882.
198.Doyle, M.P.; Forbes, D.C. “Recent Advances in Asymmetric Catalytic Metal Carbene Transformations” Chem. Rev. 1998, 98, 911-935. (invited review)
197.Roos, G.H.P.; Raab, C.E.; Emslie, N.D.; Doyle, M.P.; Lynch, V. “Synthesis, Structure, and Reactivity of a Novel Series of Diastereomeric Dirhodium(II) Tetracarboxamidates. Catalysts for Asymmetric Diazoacetate Transformations” Austral. J. Chem. 1998, 51, 1-8.
196.Doyle, M.P., Peterson, C.S.; Protopopova, M.N.; Marnett, A.B.; Parker, Jr., D.L.; Ene, D.G.; Lynch, V. “Macrocycle Formation by Catalytic Intramolecular Cyclopropanation. A New General Methodology for the Synthesis of Macrolides” J. Am. Chem. Soc. 1997, 119, 8826-8837.
195.Doyle, M.P.; Forbes, D.C.; Protopopova, M.N.; Stanley, S.A.; Vasbinder, M.M.; Xavier, K.R. “Stereocontrol in Intermolecular Dirhodium(II) Catalyzed Carbonyl Ylide Formation and Reactions. Dioxolanes and Dihydrofurans” J. Org. Chem. 1997, 62, 7210-7215.
194.Doyle, M.P.; Peterson, C.S. “Macrocyclic Oxonium Ylide Formation and Internal [2,3]-Sigmatropic Rearrangement. Catalyst Influence on Selectivity” Tetrahedron Lett. 1997, 38, 5265-5268.
193.Doyle, M.P., Ene, D.G.; Forbes, D.C.; Tedrow, J.S. “Highly Enantioselective Oxonium Ylide Formation and Stevens Rearrangement Catalyzed by Chiral Dirhodium(II) Carboxamidates” Tetrahedron Lett. 1997, 38, 4367-4370.
192.Brünner, H.; Blüchel, C.; Doyle, M.P. “Asymmetric Catalysis. Part 108. Copper Catalysts with Optically Active Ligands in the Enantioselective Meerwein Arylation of Activated Olefins” J. Organometal. Chem. 1997, 541, 89-95.
191.Doyle, M.P.; Eismont, M.E.; Zhou, Q.-L. “Enantiocontrol in Intramolecular Cyclopropanation of Diazo Ketones. Conformational Control of Metal Carbene Alignment” Russ. Chem. Bull. 1997, 46, 955-958.
190.Doyle, M.P.; McKervey, M.A. “Recent Advances in Enantioselective Syntheses Involving Diazocarbonyl Intermediates” J. Chem. Soc., Chem. Commun. 1997, 983-989. (feature article)
189.Doyle, M.P., Raab, C.E.; Roos, G.H.P.; Lynch, V.; Simonsen, S.H. “(4,0)-Dirhodium(II) Tetrakis[methyl 1-acetyl-2-oxoimidazolidin-4(S)-carboxylate]. Implications for the Mechanism of Ligand Exchange Reactions” Inorg. Chim. Acta 1997, 266, 13-18.
188.Doyle, M.P.; Peterson, C.S.; Zhou, Q.-L.; Nishiyama, H. “Comparative Evaluation of Enantiocontrol for Intramolecular Cyclopropanation of Diazoacetates with Chiral Cu(I), Rh(II), and Ru(II) Catalysts” J. Chem. Soc., Chem. Commun. 1997, 211-212.
187.Bode, J.W.; Doyle, M.P.; Protopopova, M.N.; Zhou, Q.-L. “Intramolecular Regioselective Insertion into Unactivated Prochiral Carbon-Hydrogen Bonds with Diazoacetates Catalyzed by Chiral Dirhodium(II) Carboxamidates. Highly Enantioselective Total Synthesis of Natural Lignan Lactones” J. Org. Chem. 1996, 61, 9146-9155.
186.Buck, R.T.; Doyle, M.P., Drysdale, M.J.; Ferris, L.; Forbes, D.C.; Haigh, D.; Moody, C.J.; Pearson, N.D.; Zhou, Q.-L. “Asymmetric Rhodium Carbenoid Insertion into the Si-H Bond” Tetrahedron Lett. 1996, 37, 7631-7634.
185.Doyle, M.P., Kalinin, A.V.; Ene, D.G. “Chiral Catalyst Controlled Diastereoselection and Regioselection in Intramolecular Carbon-Hydrogen Insertion Reactions of Diazoacetates” J. Am. Chem. Soc. 1996, 118, 8837-8846.
184.Doyle, M.P., Zhou, Q.-L.; Raab, C.E.; Roos, G.H.P.; Simonsen, S.H.; Lynch, V. “Synthesis and Structures of (2,2-cis)-Dirhodium(II) Tetrakis[methyl 1-acyl-2-oxoimidazolidin-4(S)-carboxylates]. Chiral Catalysts for Highly Stereoselective Metal Carbene Transformations” Inorg. Chem. 1996, 35, 6064-6073.
183.Doyle, M.P.; Protopopova, M.N.; Peterson, C.S.; Vitale, J.P.; McKervey, M.A.; Garcia, C.F. “Formation of Macrocycles by Catalytic Intramolecular Aromatic Cycloaddition of Metal Carbenes to Remote Arenes” J. Am. Chem. Soc. 1996, 118, 7865-7866.
182.Doyle, M.P., Zhou, Q.-L.; Simonsen, S.H.; Lynch V. “Dirhodium(II) Tetrakis[alkyl 2-oxaazetidine-4(S)-carboxylates]. A New Set of Effective Chiral Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions with Diazoacetates” Synlett 1996, 697-698.
181.Doyle, M.P., Zhou, Q.-L.; Charnsangavej, C.; Longoria, M.A.; McKervey, M.A.; Garcia, C.F. “Chiral Catalysts for Enantioselective Intermolecular Cyclopropanation Reactions with Methyl Phenyldiazoacetate. Origin of the Solvent Effect in Reactions Catalyzed by Homochiral Dirhodium(II) Prolinates” Tetrahedron Lett. 1996, 37, 4129-4132.
180.Doyle, M.P., Peterson, C.S.; Parker, Jr., D.L. “Formation of Macrocyclic Lactones by Enantioselective Intramolecular Cyclopropanation of Diazoacetates Catalyzed by Chiral Copper(I) and Rhodium(II) Compounds” Angew. Chem. Int. Ed. Engl. 1996, 35, 1334-1336; Angew. Chem.1996, 108, 1439-1440.
179.Doyle, M.P. “Chiral Dirhodium Carboxamidates. Catalysts for Highly Enantioselective Syntheses of Lactones and Lactams” Aldrichimica Acta 1996, 29 (1), 3-11.
178.Doyle, M.P.; Kalinin, A.V. “Highly Enantioselective Intramolecular Cyclopropanation Reactions of N-Allylic-N-methyldiazoacetamides Catalyzed by Chiral Dirhodium(II) Carboxamidates” J. Org. Chem. 1996, 61, 2179-2184.
177.Doyle, M.P.; Kalinin, A.V. “Synthesis of Pyrrolizidine Bases by Highly Diastereoselective and Regioselective Catalytic Carbon-Hydrogen Insertion Reactions of Chiral Pyrrolidinediazo-acetamides” Tetrahedron Lett. 1996, 37, 1371-1374.
176.Doyle, M.P., Winchester, W.R.; Protopopova, M.N.; Kazala, A.P.; Westrum, L.J. “(1R,2S)-(-)-6,6-Dimethyl-3-oxabicyclo[3.1.0]hexan-2-one. Highly Enantioselective Intramolecular Cyclopropanation Catalyzed by Dirhodium(II) Tetrakis[methyl 2-Pyrrolidone-5(R)-Carboxylate}” Organic Synthesis1996, 73, 13-24. (invited procedure)
175.Doyle, M.P.; Protopopova, M.N.; Zhou, Q.-L.; Bode, J.W.; Simonsen, S.H.; Lynch, V. “Optimization of Enantiocontrol for Carbon-Hydrogen Insertion with Chiral Dirhodium(II) Carboxamidates. Synthesis of Natural Dibenzylbutyrolactone Lignans from 3-Aryl-1-propyl Diazoacetates in High Optical Purity” J. Org. Chem. 1995, 60, 6654-6655.
174.Doyle, M.P.; Zhou, Q.-L.; Dyatkin, A.B.; Ruppar, D.A. “Enhancement of Enantiocontrol/ Diastereocontrol in Catalytic Intramolecular Cyclopropanation and Carbon-Hydrogen Insertion Reactions of Diazoacetates with Rh2(4S-MPPIM)4” Tetrahedron Lett. 1995, 36, 7579-7582.
173.Doyle, M.P.; Kalinin, A.V. “Enantiomer Differentiation in Intramolecular Carbon-Hydrogen Insertion Reactions of Racemic Secondary Alkyl Diazoacetates Catalyzed by Chiral Dirhodium(II) Carboxamidates” Russ. Chem. Bull. 1995, 44, 1729-1734.
172.Doyle, M.P.; Kalinin, A.V. “Highly Enantioselective Route to β-Lactams via Intramolecular C-H Insertion Reactions of Diazoacetylazacycloalkanes Catalyzed by Chiral Dirhodium(II) Carboxamidates” Synlett 1995, 1075-1076.
171.Doyle, M.P.; Dyatkin, A.B.; Kalinin, A.V.; Ruppar, D.A.; Martin, S.F.; Spallar, M.R.; Liras, S. “Highly Selective Enantiomer Differentiation in Intramolecular Cyclopropanation Reactions of Racemic Secondary Allylic Diazoacetates” J. Am. Chem. Soc. 1995, 117, 11021-11022.
170.Doyle, M.P.; Zhou, Q.-L. “Enantioselective Catalytic Intramolecular Cyclopropanation of Allylic α-Diazopropionates Optimized with Dirhodium(II) Tetrakis[methyl 2-oxazolidinone-4(S or R)-carboxylate]” Tetrahedron: Asymmetry 1995, 6, 2157-2160.
169.Doyle, M.P., Zhou, Q.-L.; Raab, C.E.; Roos, G.H.P. “Improved Enantioselection for Chiral Dirhodium(II) Carboxamide-Catalyzed Carbon-Hydrogen Insertion Reactions of Tertiary Alkyl Diazoacetates” Tetrahedron Lett. 1995, 36, 4745-4748.
168.Doyle, M.P., Protopopova, M.N.; Poulter, C.D.; Rogers, D.H. “Macrocyclic Lactones from Dirhodium(II) Catalyzed Intramolecular Cyclopropanation and Carbon-Hydrogen Insertion” J. Am. Chem. Soc. 1995, 117, 7281-7282.
167.Doyle, M.P. and Dyatkin, A.B. “Spirolactones from Dirhodium(II) – Catalyzed Diazo Decomposition with Regioselective Carbon-Hydrogen Insertion” J. Org. Chem. 1995, 60, 3035-3038.
166.Doyle, M.P., Austin, R.E.; Bailey, A.S.; Dwyer, M.P.; Dyatkin, A.B.; Kalinin, A.V.; Kwan, M.M.Y.; Liras, S.; Oalmann, C.J.; Pieters, R.J.; Protopopova, M.N.; Raab, C.E.; Roos, G.H.P.; Zhou, Q.-L.; Martin, S.F. “Enantioselective Intramolecular Cyclopropanations of Allylic and Homoallylic Diazoacetates and Diazoacetamides Using Chiral Dirhodium(II) Carboxamide Catalysts” J. Am. Chem. Soc. 1995, 117, 5763-5775.
165.Doyle, M.P.; Dyatkin, A.B.; Protopopova, M.N.; Yang, C.I.; Miertschin, C.S.; Winchester, W.R.; Simonsen, S.H.; Lynch, V.; Ghosh, R. “Enhanced Enantiocontrol in Catalytic Metal Carbene Transformations with Dirhodium(II) Tetrakis[methyl 2-oxazolidinone-4(S)-carboxylate], Rh2(4S-MEOX)4Recueil Trav. Chim. Pays-Bas 1995, 114, 163-170. (Chirality issue, invited contribution) (featured on the cover)
164.Müller, P.; Baud, C.; Ene, D.; Motallebi, S.; Doyle, M.P.; Brandes, B.D.; Dyatkin, A.B.; See, M.M. “Enantio- and cis/trans-Selectivity in Dirhodium(II)-Catalyzed Addition of Diazoacetates to Olefins” Helv. Chim. Acta 1995, 78, 459-470.
163.Doyle, M.P.; Dyatkin, A.B.; Autry, C.L. “A New Catalytic Transformation of Diazo Esters. Hydride Abstraction in Dirhodium(II) Catalyzed Reactions” J. Chem. Soc., Perkin Trans.1 1995, 619-621.
162.Doyle, M.P. “Asymmetric Syntheses with Catalytic Enantioselective Metal Carbene Transformations” Russ. Chem. Bull. (Izvestiya Akademii Nauk., Ser. Khim.) 1994, 43, 1770-1782. (invited review)
161.Doyle, M.P. “Highly Enantioselective Syntheses from Diazocarbonyl Compounds Catalyzed by Chiral Dirhodium(II) Carboxamides,” Chimica Oggi (Chemistry Today), Nov./Dec. issue 1994, 12, 13-20. (invited review)
160.Devora, G.A.; Doyle, M.P. “Highly Efficient Olefin Isomerization Catalyzed by Metal Hydrides Derived from Dirhodium(II) Carboxylates and Catecholborane” Main Group Metal Chemistry 1994, 7, 395-398. (special issue for undergraduate research)
159.Ye, T.; McKervey, M.A.; Brandes, B.D.; Doyle, M.P. “Stereoselective Synthesis of Disubstituted 3(2H)-Furanones via Catalytic Intramolecular C-H Insertion Reactions of α-Diazo-β-keto Esters Including Asymmetric Induction” Tetrahedron Lett. 1994, 35, 7269-7272.
158.Doyle, M.P., Protopopova, M.N.; Müller, P.; Ene, D.; Shapiro, E.A. “Effective Uses of Dirhodium(II) Tetrakis[methyl 2-pyrrolidone-5(R or S)-carboxylate] for Highly Enantioselective Intramolecular Cyclopropenation Reactions” J. Am. Chem. Soc. 1994, 116, 8492-8498.
157.Doyle, M.P., Shanklin, M.S.; Zlokazov, M.V. “Regioselective Hydroformylation of Alkenes Catalyzed by Di(μ-carboxylato)rhodium(I) Complexes” Synlett 1994, 615-616.
156.Doyle, M.P., Winchester, W.R.; Simonsen, S.H.; Ghosh, R. “Dirhodium(II) Tetrakis[N,N-dimethyl-2-pyrrolidone-5(S)-carboxamide]. Structural Effects on Enantioselection in Metal Carbene Transformations” Inorg. Chim. Acta 1994, 220, 193-196. (symposium-in-print, invited contribution)
155.Doyle, M.P., Dyatkin, A.B.; Tedrow, J.S. “Synthesis of 2-Deoxyxylolactone from Glycerol Derivatives via Highly Enantioselective Carbon-Hydrogen Insertion Reactions” Tetrahedron Lett. 1994, 35, 3853-3856.
154.Doyle, M.P., Dyatkin, A.B.; Roos, G.H.P.; Cañas, F.; Pierson, D.A.; van Basten, A.; Müller, P.; Polleux, P. “Diastereocontrol for Highly Enantioselective Carbon-Hydrogen Insertion Reactions” J. Am. Chem. Soc. 1994, 116, 4507-4508.
153.Doyle, M.P., Eismont, M.Y.; Protopopova, M.N.; Kwan, M.M.Y. “Enantioselective Intramolecular Cyclopropanation of N-Allylic- and N-Homoallylic Diazoacetamides Catalyzed by Chiral Dirhodium(II) Catalysts” Tetrahedron, 1994, 50, 1665-1674 (symposium-in-print, invited contribution); also 1994, 50, 4519-4528.
152.Doyle, M.P.; Shanklin, M.S. “Highly Regioselective and Stereoselective Silylcarbonylation of Alkynes Under Mild Conditions Promoted by Dirhodium(II) Perfluorobutyrate” Organometal. 1994, 13, 1081-1088.
151.Doyle, M.P.; Winchester, W.R.; Protopopova, M.N.; Müller, P.; Bernardinelli, G.; Ene, D.; Motallebi, S. “Dirhodium(II) Tetrakis[4(S)-phenyloxazolidinone] and its Catalytic Applications for Metal Carbene Transformations” Helv. Chim. Acta. 1993, 76, 2227-2235.
150.Doyle, M.P.; Oon, S.-M.; van der Heide, F.; Brown, C.B. “γ-Lactam Formation via Rhodium(II) Catalyzed Carbon-Hydrogen Insertion Reactions of γ-Diazo Amides” Bioorg. & Med. Chem. Lett. 1993, 3, 2409-2414. (symposium-in-print, invited contribution)
149.Doyle, M.P.; Winchester, W.R.; Hoorn, J.A.A.; Lynch, V.; Simonsen, S.H.; Ghosh, R. “Dirhodium(II) Tetrakis(carboxamidates) with Chiral Ligands. Structure and Selectivity in Catalytic Metal Carbene Transformations” J. Am. Chem. Soc. 1993, 115, 9968-9978.
148.Padwa, A.; Austin, D.J.; Price, A.T.; Semones, M.A.; Doyle, M.P.; Protopopova, M.N.; Winchester, W.R.; Tran, A. “Ligand Effects on Dirhodium(II)-Carbene Reactivities. Highly Effective Switching Between Competitive Carbenoid Transformations” J. Am. Chem. Soc. 1993, 115, 8669-8680.
147.Doyle, M.P.; Plummer, B.F. “Replacing Mineral Acids in the Laboratory. Nafion® NR50 Catalyzed Dehydration and Esterification Reactions” J. Chem. Educ. 1993, 70, 493-495.
146.Doyle, M.P.; Westrum, L.J.; Protopopova, M.N.; Eismont, M.Y.; Jarstfer, M.B. “Dirhodium(II) Tetraacetate Catalyzed Hydroboration of Alkenes” Mendeleev Commun. 1993, 81-82.
145.Doyle, M.P.; Protopopova, M.N.; Brandes, B.D.; Davies, H.M.L.; Huby, N.J.S.; Whitesell, J.K. “Diastereoselectivity Enhancement in Cyclopropanation and Cyclopropenation Reactions of Chiral Diazoacetate Esters Catalyzed by Chiral Dirhodium(II) Carboxamides” Synlett. 1993, 151-153.
144.Doyle, M.P.; Shanklin, M.S. “Highly Efficient Regioselective Silylcarbonylation of Alkynes Catalyzed by Dirhodium(II) Perfluoroborate” Organometal.1993, 12, 11-12.
143.Doyle, M.P.; Westrum, L.J.; Wolthuis, W.N.E.; See, M.M.; Boone, W.P.; Bagheri, V.; Pearson, M.M. “Electronic and Steric Control in Carbon-Hydrogen Insertion Reactions of Diazoacetoacetates Catalyzed by Dirhodium(II) Carboxylates and Carboxamides” J. Am. Chem. Soc. 1993, 115, 958-964.
142.Doyle, M.P.; Eismont, M.Y.; Bergbreiter, D.E.; Gray, H.N. “Enantioselective Metal Carbene Transformations with Polyethylene-Bound Soluble Recoverable Dirhodium(II) 2-Pyrrolidone-5(S)-carboxylate” J. Org. Chem. 1992, 57, 6103-6105.
141.Doyle, M.P.; Protopopova, M.N.; Winchester, W.R.; Daniel, K.L. “Enantiocontrol and Regiocontrol in Lactam Syntheses by Intramolecular Carbon-Hydrogen Insertion Reactions of Diazoacetamides Catalyzed by Chiral Rhodium(II) Carboxamides” Tetrahedron Lett. 1992, 33, 7819-7822.
140.McCarthy, N.; McKervey, M.A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M.P. “Rhodium(II) Binaphthylphosphate – A New Catalyst for Diazocarbonyl Reactions Including Asymmetric Synthesis” Tetrahedron Lett. 1992, 33, 5983-5986.
139.Protopopova, M.N.; Doyle, M.P.; Müller, P.; Ene, D. “High Enantioselectivity for Intermolecular Cyclopropenation of Alkynes by Diazo Esters Catalyzed by Chiral Dirhodium(II) Carboxamides” J. Am. Chem. Soc. 1992, 114, 2755-2757.
138.Padwa, A.; Austin, D.J.; Hornbuckle, S.F.; Semones, M.A.; Doyle, M.P.; Protopopova, M.N. “Control of Chemoselectivity in Catalytic Carbenoid Reactions,” J. Am. Chem. Soc. 1992, 114, 1874-1876.
137.Doyle, M.P. “The Future of Chemistry Education in the United States,” Boletin Soc. Chilena Quim. 1992, 37, 251-257.
136.Doyle, M.P.; Devora, G.A.; Nefedov, A.O.; High, K.G. “Addition/Elimination in the Rhodium(II) Perfluorobutyrate Catalyzed Hydrosilylation of 1-Alkenes. Rhodium Hydride Promoted Isomerization and Hydrogenation” Organometal. 1992, 11, 549-555.
135.Doyle, M.P.; van Oeveren, A.; Westrum, L.J.; Protopopova, M.N.; Clayton, Jr., T.W. “Asymmetric Synthesis of Lactones with High Enantioselectivity by Intramolecular Carbon-Hydrogen Insertion of Alkyl Diazoacetates Catalyzed by Chiral Rhodium(II) Carboxamides” J. Am. Chem. Soc. 1991, 113, 8982-8984
134.Doyle, M.P. “Chiral Catalysts for Enantioselective Carbenoid Cyclopropanation Reactions” Recueil Trav. Chim. Pays-Bas 1991, 110, 305-316. (review)
133.Smith, R.C.; Gore, J.Z.; Doyle, M.P. “Degradation of Uric Acid During Autocatalytic Oxidation of Oxyhemoglobin Induced by Sodium Nitrite” J. Free Radicals in Biology and Medicine 1991, 11, 373-377.
132.Doyle, M.P.; High, K.G.; Nesloney, C.L.; Clayton, Jr., T.W.; Lin, J. “Rhodium(II) Perfluorobutyrate Catalyzed Hydrosilylation of 1-Alkynes. Trans Addition and Rearrangement to Allylsilanes” Organometal. 1991, 10, 1225-1226.
131.Doyle, M.P.; Pieters, R.J.; Martin, S.F.; Austin, R.E.; Oalmann, C.J.; Müller, P. “High Enantioselectivity in the Intramolecular Cyclopropanation of Allyl Diazoacetates Using a Novel Rhodium(II) Catalyst” J. Am. Chem. Soc. 1991, 113, 1423-1424.
130.Doyle, M.P.; Pieters, R.J.; Taunton, J.; Pho, H.Q.; Padwa, A.; Hertzog, D.L.; Precedo, L. “Synthesis of Nitrogen Containing Polycycles Via Rhodium(II) Induced Cyclization-Cycloaddition and Insertion Reactions of N-(Diazoacetoacetyl)amides. Conformational Control of Reaction Selectivity” J. Org. Chem. 1991, 56, 820-829.
129.Doyle, M.P.; Brandes, B.D.; Kazala, A.P.; Pieters, R.J.; Jarstfer, M.B.; Watkins, L.M.; Eagle, C.T. “Chiral Rhodium(II) Carboxamides. A New Class of Catalysts for Enantioselective Cyclopropanation Reactions” Tetrahedron Lett. 1990, 31, 6613-6616.
128.Doyle, M.P.; High, K.G.; Bagheri, V.; Pieters, R.J.; Lewis, P.J.; Pearson, M.M. “Rhodium(II) Perfluorobutyrate Catalyzed Silane Alcoholysis. A Highly Selective Route to Silyl Ethers” J Org. Chem. 1990, 55, 6082-6086.
127.Brunner, H., Wutz, K.; Doyle, M.P. “Asymmetrische Katalysen. 58. Enantioselective S-H- and C-H-Insertionen mit Optisch Aktiven Rh(II)- und Cu(II)-Katalysatoren” Montash Chem. 1990, 121, 755-764.
126.Müller, P.; Pautex, N.; Doyle, M.P.; Bagheri, V. “Rh(II) Catalyzed Isomerizations of Cyclopropenes. Evidence for Rh(II)-complexed Vinylcarbene Intermediates” Helv. Chim. Acta1990, 73, 1233-1241.
125.Doyle, M.P.; Bagheri, V.; Wandless, T.J.; Harn, N.K.; Brinker, D.A.; Eagle, C.T.; Loh, K.-L. “Exceptionally High Trans(anti) Stereoselectivity in Catalytic Cyclopropanation Reactions” J. Am. Chem. Soc. 1990, 112, 1906-1912.
124.Doyle, M.P.; Bagheri, V.; Claxton, E.E. “Synthesis of Allenes by [2,3]-Sigmatropic Rearrangement of 2-Propyn-1-yl Oxonium Ylides Formed in Rhodium(II) Carboxylate Catalyzed Reactions of Diazo Compounds” J. Chem. Soc., Chem. Commun. 1990, 46-48.
123.Doyle, M.P.; Bagheri, V.; Pearson, M.M.; Edwards, J.D. “Highly Selective γ-Lactone Syntheses by Intramolecular Carbenoid Carbon-Hydrogen Insertion in Rhodium(II) Carboxylate and Rhodium(II) Carboxamide Catalyzed Reactions of Diazo Esters” Tetrahedron Lett. 1989, 30, 7001-7004.
122.Doyle, M.P.; Taunton, J.; Pho, H.Q. “Conformational and Electronic Preferences in Rhodium(II) Carboxylate and Rhodium(II) Carboxamide Catalyzed Carbon-Hydrogen Insertion Reactions of N,N-Disubstituted Diazoacetoacetamides” Tetrahedron Lett. 1989, 30, 5397-5400.
121.Doyle, M.P.; Nesloney, C.L.; Shanklin, M.S.; March, C.A.; Brown, K.C. “Formation and Characterization of 3-O-Arenediazoascorbic Acids. New Stable Diazo Ethers” J. Org. Chem. 1989, 54, 3785-3789.
120.Doyle, M.P.; High, K.G.; Oon, S.-M.; Osborn, A.K. “Diazirines in Carbenoid Reactions Catalyzed by Rhodium(II) Carboxylates” Tetrahedron Lett.1989, 30, 3049-3052.
119.Pladziewicz J.R.; Doyle, M.P. “Application of Marcus Theory to One-Electron Outer-Sphere Electron Transfer Reactions of Benzenediazonium Salts” J. of Imaging Science 1989, 33, 57-61.
118.Jackson, J.E.; Soundararajan, N.; Platz, M.S.; Doyle, M.P.; Liu, M.T.H. “Activation Parameters for the Reaction of Phenylchlorocarbene with Pyridine, Tri-n-butyltin Hydride, and Triethylsilane: Evidence Against the Need to Invoke Reversibly Formed Complexes in the Reaction of This Carbene with Olefins” Tetrahedron Lett. 1989, 30, 1335-1338.
117.Doyle, M.P. “Tailors, Targets, and Traditions in Undergraduate Research” Forum for Honors 1988, XVIII (No. 4), 6-12.
116.Bagheri, V.; Doyle, M.P.; Taunton, J.; Claxton, E.E. “A New and General Synthesis of α-Silyl Carbonyl Compounds by Si-H Insertion from Transition Metal Catalyzed Reactions of Diazo Esters and Diazo Ketones” J. Org. Chem. 1988, 53, 6158-6160.
115.Doyle, M.P.; Taunton, J.; Oon, S.-M.; Liu, M.T.H.; Soundararajan, N.; Platz, M.S.; Jackson, J.E. “Reactivity and Selectivity in Intermolecular Insertion Reactions of Chlorophenylcarbene” Tetrahedron Lett. 1988, 29, 5863-5866.
114.Doyle, M.P.; Bagheri, V.; Harn, N.K. “Facile Catalytic Methods for Intermolecular Generation of Allylic Oxonium Ylides and their Stereoselective [2,3]-Sigmatropic Rearrangement” Tetrahedron Lett. 1988, 29, 5119-5122.
113.Soundararajan, N.; Platz, M.S.; Jackson, J.E.; Doyle, M.P.; Oon, S.-M.; Liu, M.T.H.; Anand, S.M. “Addition of Arylchlorocarbenes to α,β-Unsaturated Esters. Absolute Rates, Substituent Effects, and Variable Reactivities” J. Am. Chem. Soc. 1988, 110, 7143-7152.
112.Doyle, M.P.; Shanklin, M.S.; Oon, S.-M.; Pho, H.Q.; van der Heide, F.R.; Veal, W.R. “Construction of β-Lactams by Highly Selective Intramolecular C-H Insertion from Rhodium(II) Carboxylate Catalyzed Reactions of Diazoacetamides” J. Org. Chem. 1988, 53, 3384-3386.
111.Brown, K.C.; Doyle, M.P. “Reduction of Arenediazonium Salts by Hydroquinone. Kinetics and Mechanism for the Electron-Transfer Step” J. Org. Chem. 1988, 53, 3255-3261.
110.Doyle, M.P.; Shanklin, M.S.; Pho, H. Q. “Cycloheptatriene Synthesis through Rhodium(II) Acetate-Catalyzed Intramolecular Addition Reactions of N-Benzyldiazoacetamides” Tetrahedron Lett. 1988, 29, 2639-2642.
109.Doyle, M.P.; Shanklin, M.S.; Pho, H.Q.; Mahapatro, S.N. “Rhodium(II) Acetate and Nafion-H Catalyzed Decomposition of N-Aryldiazoamides. An Efficient Synthesis of 2(3H)-Indolinones” J. Org. Chem. 1988, 53, 1017-1022.
108.Doyle, M.P.; Mahapatro, S.N.; Broene, R.D.; Guy, J.K. “Oxidation and Reduction of Hemoproteins by Trioxodinitrate(II). The Role of Nitrosyl Hydride and Nitrite” J. Am. Chem. Soc. 1988, 110, 593-599.
107.Doyle, M.P.; Mahapatro, S.N.; Guy, J.K.; Hester, M.R.; VanZyl, C.M.; Boundy, K.L. “Electron Transfer Between Hemoglobin and Arenediazonium Salts. Mechanism of Heme Aryl-Iron Complex Formation” Inorg. Chem. 1987, 26, 3387-3392.
106.Doyle, M.P.; Mahapatro, S.N.; Caughey, A.C.; Chinn, M.S.; Colsman, M.R.; Harn, N.K.; Redwine, A.E. “Olefin Coordination with Rhodium(II) Perfluoroalkanoates in Solution” Inorg. Chem. 1987, 26, 3070-3072.
105.Doyle, M.P.; Devia, A.H.; Bassett, K.E.; Terpstra, J.W.; Mahapatro, S.N. “Unsymmetrical Alkenes by Carbene Coupling from Diazirine Decomposition in the Presence of Diazo Compounds” J. Org. Chem. 1987, 52, 1619-1621.
104.Liu, M.T.H.; Doyle, M.P.; Loh, K.-L. “Catalysis of Olefin Isomerization by Tight Ion Pairs” J. Org. Chem. 1987, 52, 323-324.
103.Doyle, M.P.; Guy, J.K.; Brown, K.C.; VanZyl, C.M.; Mahapatro, S.N.; Pladziewicz, J.R. “Outer-Sphere One-Electron Reductions of Arenediazonium Salts” J. Am. Chem. Soc. 1987, 109, 1536-1540.
102.Doyle, M.P.; Loh, K.-L.; DeVries, K.; Chinn, M.S. “Enhancement of Stereoselectivity in Catalytic Cyclopropanation Reactions” Tetrahedron Lett.1987, 28, 833-836.
101.Doyle, M.P. “Electrophilic Metal Carbenes as Reaction Intermediates in Catalytic Reactions” Acc. Chem. Res. 1986, 19, 348-356.
100.Doyle, M.P. “Catalytic Methods for Metal Carbene Transformations” Chem. Rev. 1986, 86, 919-939. (special thematic issue on “Emerging Organic Reactions”)
99.Doyle, M.P.; Loh, K.-L.; Nishioka, L.I.; McVickar, M.B., Liu, M.T.H. “Formation of a Dipolar Adduct in the Reaction of Arylchlorocarbenes with Diethyl Maleate” Tetrahedron Lett. 1986, 27, 4395-4398.
98.Doyle, M.P.; Mahapatro, S.N., VanZyl, C.M.; Hester, M.R. “Electron Transfer in the Heme Pocket of Hemoglobin” J. Am. Chem. Soc. 1985, 107, 6136-6137.
97.Doyle, M.P.; Herman, J.G.; Dykstra, R.L. “Autocatalytic Oxidation of Hemoglobin Induced by Nitrite: Activation and Chemical Inhibition” J. Free Radicals in Biology and Medicine 1985, 1, 145-153.
96.Doyle, M.P.; Dorow, R.L.; Terpstra, J.W.; Rodenhouse, R.A. “Synthesis and Catalytic Reactions of Chiral N-Diazoacetyloxazolidones” J. Org. Chem.1985, 50, 1663-1666.
95.Doyle, M.P.; Griffin, J.H.; da Coñceicao, J. “Procatalysts for Carbenoid Transformations” J. Chem. Soc., Chem. Commun. 1985, 328-329.
94.Doyle, M.P.; Colsman, M.R.; Chinn, M.S. “Olefin Coordination with Rhodium(II) Trifluoroacetate” Inorg. Chem. 1984, 23, 3684-3685.
93.Nocek, J.M.; Kurtz, Jr., D.M.; Pickering, R.A.; Doyle, M.P. “Oxidation of Deoxyhemerythrin to the Semi-Met Level by Nitrite” J. Biol. Chem. 1984, 29, 12334-12338.
92.Doyle, M.P. “Research as Chemical Education” J. Chem. Educ. 1984, 61, 854-856.
91.Doyle, M.P.; Wang, L.C.; Loh, K.-L. “Influence of Olefin Coordination on Cyclopropanation Selectivity” Tetrahedron Lett. 1984, 25, 4087-4090.
90.Doyle, M.P.; Mahapatro, S.N. “Nitric Oxide Dissociation from Trioxodinitrate(II) in Aqueous Solution” J. Am. Chem. Soc. 1984, 106, 3678-3679.
89.Doyle, M.P.; Terpstra, J.W.; Winter, C.H.; Griffin, J.H. “Rhodium(II) Acetate Catalyzed Hydrocarbon Oxidations by Molecular Oxygen” J. Molec. Catal. 1984, 26, 259-266.
88.Doyle, M.P.; Griffin, J.H.; Chinn, M.S.; van Leusen, D. “Rearrangements of Ylides Generated from Reactions of Diazo Compounds with Allyl Acetals and Thioketals by Catalytic Methods. Heteroatom Acceleration of the [2,3]-Sigmatropic Rearrangement” J. Org. Chem. 1984, 49, 1917-1925.
87.Doyle, M.P.; Mahapatro, S.N.; Van Tran, S. “Oxidation of Hemoglobin by Arenediazonium Salts. The Influence of Dioxygen” Inorg. Chim. Acta1984, 92, 123-129.
86.Doyle, M.P.; Trudell, M.L. “Catalytic Role of Copper Triflate in Lewis Acid Promoted Reactions of Diazo Compounds” J. Org. Chem. 1984, 49, 1196-1199.
85.Doyle, M.P.; Terpstra, J.W.; Winter, C.H. “Nucleophilic Character of an Electrophilic Carbene. Synthesis of Cyclopropanes by Thermal Decomposition of 3-Chloro-3-phenyldiazirine” Tetrahedron Lett. 1984, 25, 901-904.
84.Doyle, M.P.; Pickering, R.A.; da Coñceicao, J. “Structural Effects in Alkyl Nitrite Oxidation of Human Hemoglobin” J. Biol. Chem. 1984, 259, 80-87.
83.Doyle, M.P.; Griffin, J.H.; Bagheri, V.; Dorow, R.L. “Correlations Between Catalytic Reactions of Diazo Compounds and Stoichiometric Reactions of Transition Metal Carbenes with Alkenes. Mechanism of the Cyclopropanation Reaction” Organometal. 1984, 3, 53-61.
82.Doyle, M.P.; Dorow, R.L.; Buhro, W.E.; Griffin, J.H.; Tamblyn, W.H.; Trudell, M.L. “Stereoselectivity of Catalytic Cyclopropanation Reactions. Catalyst Dependence in Reactions of Ethyl Diazoacetate with Alkenes” Organometal. 1984, 3, 44-52.
81.Doyle, M.P.; Trudell, M.L. “Homologation of Acetals of α,β-Unsaturated Carbonyl Compounds with Diazoesters. Synthesis of Acetals of β,γ-Unsaturated Carbonyl Compounds” J. Org. Chem. 1983, 48, 5146-5148.
80.Doyle, M.P.; Terpstra, J.W.; Pickering, R.A.; LePoire, D.M. “Hydrolysis, Nitrosyl Exchange, and Synthesis of Alkyl Nitrites” J. Org. Chem. 1983, 48, 3379-3382.
79.Doyle, M.P.; Pickering, R.A.; Cook, B.R. “Oxidation of Oxymyoglobin by Nitric Oxide through Dissociation from Cobalt Nitrosyls” J. Inorg. Biochem.1983, 19, 329-338.
78.Doyle, M.P.; Colsman, M.R.; Dorow, R.L. “Effective Methods for the Syntheses of 2-Pyrazolines and Pyrazoles from Diazocarbonyl Compounds” J. Heterocyclic Chem. 1983, 20, 943-946.
77.Blankespoor, R.L.; Doyle, M.P.; Smith, D.J.; Van Dyke, D.A.; Waldyke, M.J. “Chemical and Electrochemical Oxidation of O,O,O-Trisubstituted Phosphorothioates and Triphenylphosphine Sulfide” J. Org. Chem. 1983, 48, 1176-1179.
76.Doyle, M.P.; Dow, R.L.; Bagheri, V.; Patrie, W.J. “Regioselectivity in Nickel(II)-Mediated Oxidations of Diols” J. Org. Chem. 1983, 48, 476-480.
75.Doyle, M.P.; van Leusen, D. “Rearrangements of Oxocyclopropanecarboxylate Esters to Vinyl Ethers. The Disparate Behavior of Transition Metal Catalysts” J. Org. Chem. 1982, 47, 5326-5327.
74.Doyle, M.P.; Dorow, R.L.; Tamblyn, W.H. “Cyclopropanation of α,β-Unsaturated Carbonyl Compounds and Nitriles with Diazo Compounds. Nature of the Involvement of Transition Metal Promoters” J. Org. Chem. 1982, 47, 4059-4068.
73.Doyle, M.P.; Dorow, R.L.; Tamblyn, W.H.; Buhro, W.E. “Regioselectivity in Catalytic Cyclopropanation Reactions” Tetrahedron Lett. 1982, 23, 2261-2264.
72.Doyle, M.P.; Pickering, R.A.; Dykstra, R.L.; Cook, B.R. “Mechanisms of Nitrosyl Transfer. Dissociation of Nitric Oxide from Cobalt Nitrosyls” J. Am. Chem. Soc. 1982, 104, 3392-3397.
71.Doyle, M.P.; Pickering, R.A.; Dykstra, R. L.; Nelson, C.L.; Boyer, R.F. “Involvement of Peroxide and Superoxide in the Oxidation of Hemoglobin by Nitrite” Biochem. Biophys. Res. Commun. 1982, 105, 127-132.
70.Doyle, M.P.; van Leusen, D. “Transition Metal Catalyzed Rearrangements of Oxocyclopropanes to Vinyl Ethers. Activation by Vicinal Carboalkoxy Substituents” J. Am. Chem. Soc. 1981, 103, 5917-5719.
69.Blankespoor, R.L.; Doyle, M.P.; Hedstrand, D.M.; Tamblyn, W.H.; Van Dyke, D.A. “Formation and Reactions of Dithiodicarbenium Salts” J. Am. Chem. Soc. 1981, 103, 7096-7101.
68.Doyle, M.P.; Tamblyn, W.H.; Bagheri, V. “Highly Effective Catalytic Methods for Ylide Generation from Diazo Compounds; Mechanism of the Rhodium and Copper Catalyzed Reactions with Allylic Compounds” J. Org. Chem. 1981, 46, 5094-5102.
67.Doyle, M.P.; Bagheri, V. “Regioselective Oxidations of Primary Alcohols in 1,4-Diols” J. Org. Chem. 1981, 46, 4806-4609.
66.Tamblyn, W.H.; Hoffman, S.R.; Doyle, M.P.; “Correlation Between Catalytic Cyclopropanation and Ylide Generation” J. Organometal. Chem. 1981, 216, C64-C68.
65.Doyle, M.P.; LePoire, D.M.; Pickering, R.A. “Oxidation of Hemoglobin and Myoglobin by Alkyl Nitrites. Inhibition by Oxygen” J. Biol. Chem. 1981, 256, 12399-12404.
64.Doyle, M.P.; Pickering, R.A.; DeWeert, T.M.; Hoekstra, J.W.; Pater, D.R. “Kinetics and Mechanism of the Oxidation of Human deoxyHemoglobin by Nitrites” J. Biol. Chem. 1981, 256, 12393-12398.
63.Doyle, M.P.; van Leusen, D.; Tamblyn, W.H. “Efficient Alternative Catalysts and Methods for the Synthesis of Cyclopropanes from Olefins and Diazo Compounds” Synthesis 1981, 787-789.
62.Doyle, M.P.; Tamblyn, W.H.; Buhro W.E.; Dorow, R.L. “Exceptionally Effective Catalysis of Cyclopropanation Reactions by the Hexarhodium Carbonyl Cluster” Tetrahedron Lett. 1981, 22, 1783-1786.
61.Doyle, M.P.; Hoekstra, J.W. “Oxidation of Nitrogen Oxides by Bound Dioxygen in Hemoproteins” J. Inorg. Biochem. 1981, 14, 351-358.
60.Doyle, M.P.; Dow, R.L. “Selective Oxidations of Alcohols by Bromine in Combination with Nickel(II) Benzoate” Synth. Commun. 1980, 10, 881-885.
59.Doyle, M.P.; Van Doornik F.J.; Funkes, C.L. “Nitrosyl Transfer to Metalloproteins. Selective Intermolecular Transfer of the Nitrosyl Group from Cobalt Nitrosyls to Hemoglobin and Myoglobin” Inorg. Chim. Acta 1980, 46, L111-L113.
58.Doyle, M.P.; Buhro, W.E.; Davidson, J.G.; Elliott, R.C.; Hoekstra J.W.; Oppenhuizen, M. “Lewis Acid Promoted Reactions of Diazocarbonyl Compounds. 3. The Synthesis of Oxazoles from Nitriles Through Intermediate β-Imidatoalkenediazonium Salts” J. Org. Chem. 1980, 45, 3657-3664.
57.Doyle, M.P.; Dow, R.L.; Bagheri, V.; Patrie, W.J. “Steric Selectivity in Oxidations of Diols” Tetrahedron Lett. 1980, 21, 2795-2798.
56.Doyle, M.P.; Van Lente, M.A.; Mowat, R.; Fobare, W.F. “Alkyl Nitrite – Metal Halide Deamination Reactions. 7. Synthetic Coupling of Electrophilic Bromination with Substitutive Deamination for Selective Synthesis of Multiply Brominated Aromatic Compounds from Arylamines” J. Org. Chem.1980, 45, 2570-2575.
55.Doyle, M.P.; Davidson, J.G. “Molybdenum Hexacarbonyl Catalyzed Cyclopropanation of α,β-Unsaturated Esters and Nitriles with Diazocarbonyl Compounds” J. Org. Chem. 1980, 45, 1538-1539.
54.Doyle, M.P.; Buhro, W.E.; Dellaria, Jr., J.F. “Lewis Acid-Promoted Cyclopropanation of α,β-Unsaturated Carbonyl Compounds By Diazocarbonyl Compounds. A Facile Synthesis of 1,2-Disubstituted Cyclopropylcarbonyl Compounds of High Isomeric Purity” Tetrahedron Lett. 1979, 4429-4432.
53.Doyle, M.P.; Patrie, W.J.; Williams S.B. “Nickel(II) Bromide – Catalyzed Oxidations of Primary and Secondary Alcohols to Carbonyl Compounds by Benzoyl Peroxide” J. Org. Chem. 1979, 44, 2955-2956.
52.Doyle, M.P.; Whitefleet, J.L.; Bosch, R.J. “Reactions of the Nitrosonium Ion. 11. Fluoride Transfer from Complex Fluoride Anions to Carbenium Ions in the Nitrosative Decomposition of Aliphatic Azides” J. Org. Chem. 1979, 44, 2923-2929.
51.Doyle, M.P.; Bryker, W.J. “Alkyl Nitrite-Metal Halide Deamination Reactions. 6. Direct Synthesis of Arenediazonium Tetrafluoroborate Salts from Aromatic Amines, tert-Butyl Nitrite, and Boron Trifluoride Etherate in Anhydrous Media” J. Org. Chem. 1979, 44, 1572-1574.
50.Doyle, M.P.; Elliott, R.C.; Dellaria, Jr., J.F. “Lewis Acid – Promoted Reactions of n-(1-Phenylcyclopropyl)alkanoyl Chlorides. Ring-size Effects in Competitive Intramolecular Acylation of Phenyl and Cyclopropyl Substituents” J. Org. Chem. 1978, 43, 4459-4461.
49.Doyle, M.P.; Bosch, R.J.; Seites, P.G. “Alkyl Nitrite-Metal Halide Deamination Reactions. 5. In Situ Generation of Nitrosyl Halides. Effective Product Control from Nitrosyl Chloride Diazotization of Primary Aliphatic Amines in N,N-Dimethylformamide” J. Org. Chem. 1978, 43, 4120-4125.
48.Doyle, M.P.; Oppenhuizen, M.; Elliott, R.C.; Boelkins, M.R. “Lewis Acid-Promoted 1,3-Dipolar Addition Reactions of Diazocarbonyl Compounds. A General Synthesis of Oxazoles” Tetrahedron Lett. 1978, 2247-2250.
47.Doyle, M.P.; McOsker, C.C. “Silane Reductions in Acidic Media. 10. Ionic Hydrogenation of Cycloalkenes. Stereoselectivity and Mechanism” J. Org. Chem. 1978, 43, 693-696.
46.Doyle, M.P.; Williams, S.B.; McOsker, C.C. “Boron Trifluoride-Catalyzed Elimination of Borate Esters. A Mild Procedure for the Preparation of Alkenes” Synthesis 1977, 717-718.
45.Doyle, M.P.; Dellaria, Jr., J.F.; Siegfried, B.; Bishop, S.W. “Reductive Deamination of Arylamines by Alkyl Nitrites in N,N-Dimethylformamide. A Direct Conversion of Arylamines to Aromatic Hydrocarbons” J. Org. Chem. 1977, 42, 3494 -3498.
44.Doyle, M.P.; Hedstrand D.M. “Reversible Oxidation of 1,3-Dithiolan-2-thione” J. Chem. Soc., Chem. Commun. 1977, 643-644.
43.Doyle, M.P.; Siegfried B.; Fobare W.F. “Nitrosative Oxidation of Arylhydrazines by Alkyl Nitrites and Copper(II) Halides” Tetrahedron Lett. 1977, 2655-2658.
42.Doyle, M.P.; Siegfried, B.; Elliott, R.C.; Dellaria, Jr., J.F. “Alkyl Nitrite-Metal Halide Deamination Reactions. 3. Arylation of Olefinic Compounds in the Deamination of Arylamines by Alkyl Nitrites and Copper(II) Halides. A Convenient and Effective Variation of the Meerwein Arylation Reaction” J. Org. Chem. 1977, 42, 2431-2436.
41.Doyle, M.P.; Siegfried, B.; Dellaria, Jr., J.F. “Alkyl Nitrite-Metal Halide Deamination Reactions. 2. Substitutive Deamination of Arylamines by Alkyl Nitrites and Copper(II) Halides. A Direct and Remarkably Efficient Conversion of Arylamines to Aryl Halides” J. Org. Chem. 1977, 42, 2426-2431.
40.Doyle, M.P.; McOsker, C.C.; Ball, N.; West, C.T. “The Effect of Lewis Acids on Stereo-selectivities in Ketone Reductions. The Principle of Complexation-Induced Conformational Perturbation. Energy Minimization in the Transition States for Hydride Transfer” J. Org. Chem. 1977, 42, 1922-1928.
39.Doyle, M.P.; Whitefleet, J.L.; DeBruyn, D.J.; Wierenga, W. “Decarboxylations of Azodicarboxylates by Nitrosonium and Nitronium Salts. Decarboxylative Oxidation and Substitution Reactions” J. Am. Chem. Soc. 1977, 99, 494-498.
38.Doyle, M.P.; West, C.T.; Donnelly, S.J.; McOsker, C.C. “Silane Reductions in Acidic Media. VIII. Boron Trifluoride Catalyzed Organosilane Reductions. Selectivity and Mechanisms” J. Organometal. Chem. 1976, 117, 129-140.
37.Doyle, M.P.; McOsker, C.C.; West, C.T. “Silane Reductions in Acidic Media. VII. Aluminum Chloride Catalyzed Hydrogen-Halogen Exchange Between Organosilanes and Alkyl Halides. An Efficient Hydrocarbon Synthesis” J. Org. Chem. 1976, 41, 1393-1396.
36.Doyle, M.P.; Siegfried, B. “Oxidative Deamination of Primary Amines: Selective Synthesis of Geminal Dihalides” J. Chem. Soc., Chem. Commun.1976, 433-434.
35.Doyle, M.P.; Siegfried, B.; Hammond, J.J. “Oxidative Deamination of Primary Amines by Copper Halide Nitrosyls. The Formation of Geminal Dihalides” J. Am. Chem. Soc. 1976, 98, 1627-1629.
34.Doyle, M.P.; Siegfried, B. “The Disproportionation of Trityl Benzyl Ethers. Kinetic Analysis of the Trityl Salt Catalyzed Reaction. Evidence for the Involvement of Ion Pairs in the Hydrogen Transfer Step” J. Am. Chem. Soc. 1976, 98, 163-166.
33.Doyle, M.P.; West, C.T. “Silane Reductions in Acidic Media. VI. The Mechanism of Organosilane Reductions of Carbonyl Compounds. Transition State Geometries of Hydride Transfer Reactions” J. Org. Chem. 1975, 40, 3835-3838.
32.Doyle, M.P.; West, C.T. “Silane Reductions in Acidic Media. V. Reductions of Alkyl-Substituted Cyclohexanones by Di- and Tri-t-butylsilanes. Steric Hindrance to Nucleophilic Attack at Silicon in the Trifluoroacetolysis of Silyl Alkyl Ethers” J. Org. Chem1975, 40, 3829-3834.
31.Doyle, M.P.; West, C.T. “Silane Reductions in Acidic Media. IV. Reductions of Alkyl-Substituted Cyclohexanones by Mono-, Di-, and Trialkylsilanes. Stereochemistry of Alcohol and Ether Formation” J. Org. Chem. 1975, 40, 3821-3829.
30.Doyle, M.P.; Whitefleet, J.L.; Zaleta, M.A. “The Nature of Fluoride Transfer from Complex Fluoride Anions to Carbenium Ions” Tetrahedron Lett.1975, 4201-4204.
29.Doyle, M.P. “Reaction Forms Geminal Dihalides” in Chemical & Engineering NewsSept. 8, 1975, 23.
28.Doyle, M.P.; Hedstrand D.; Busman, S.C.; Alexander, D. “Reactions of the Nitrosonium Ion. VIII. Reactions of Nitrosonium Tetrafluoroborate and Benzhydryl Tetrafluoroborate with Benzhydryl Azides. The Mechanism of Aldehyde and Ketone Formation” J. Am. Chem. Soc. 1975, 97, 5554-5558.
27.Doyle, M.P.; Bade, T.R. “Internal Lewis Acid Catalyzed Ring-Expansion Reactions of Cyclopropylalkanoyl Chlorides” Tetrahedron Lett. 1975, 3031-3034.
26.Doyle, M.P.; West C.T. “Hindered Organolsilicon Compounds. The Synthesis and Properties of Di-t-butyl-, Di-t-butylmethyl-, and Tri-t-butylsilanes” J. Am. Chem. Soc. 1975, 97, 3777-3782.
25.Doyle, M.P.; Zuidema L.J., Bade T.R. “Cyclic Ether Formation in Oxidations of Primary Alcohols by Cerium(IV). Reactions of 5-Phenyl-1-pentanol, 4-Phenyl-1-butanol, and 3-Phenyl-1-propanol with Ceric Ammonium Nitrate” J. Org. Chem. 1975, 40, 1454-1456.
24.Doyle, M.P.; Spoelhof G.D.; Zaleta, M.A. “Reactions of the Nitrosonium Ion. VII. Synthesis of Dihydroisoquinolines and Oxazoles from Azides in Nitrile Solvents” J. Heterocyclic Chem. 1975, 12, 263-265.
23.Doyle, M.P.; DeBruyn D.J.; Donnelly S.J.; Kooistra D.A.; Odubela A.A.; West C.T.; Zonnebelt S.M. “Silane Reductions in Acidic Media. III. General Syntheses of Alcohols, Symmetrical Ethers, Carboxylate Esters and Acetamides” J. Org. Chem. 1974, 39, 2740-2747.
22.Doyle, M.P. “A Spectrometric Study of the Oxidation of Alcohols by Cerium(IV)” J. Chem. Educ. 1974, 51, 131-132.
21.Doyle, M.P.; Kalmbacher J.G.; Wierenga W.; DeBoer J.E. “Nitrosative Cleavage of Benzalazine and Related Aldehyde Azines. Production, Decomposition and Trapping of Iminodiazonium Ions” Tetrahedron Lett. 1974, 1455-1458.
20.Doyle, M.P.; Swedo R.J.; Rocek J. “The Effect of Cerium(III) and Cerium(IV) on Chromic Acid Oxidations. The Elimination of the Chromium(IV) – Alcohol Oxidation” J. Am. Chem. Soc. 1973, 95, 8352-8357.
19.Doyle, M.P.; Raynolds P.W.; Barents R.A.; Bade T.R.; Danen W.C.; West C.T. “Free Radical Rearrangements in the Thermal Decomposition of tert-Butylperoxy 3-(1-Phenylcyclopropyl) proponoate, 4-(1-Phenylcyclopropyl)butanoate, and 5-(1-Phenylcyclopropyl)pentanoate” J. Am. Chem. Soc.1973, 95, 5988-6000.
18.West C.T.; Donelly S.J.; Kooistra D.A.; Doyle, M.P. “Silane Reductions in Acidic Media. II. Reductions of Aryl Aldehydes and Ketones by Trialkylsilanes in Trifluoroacetic Acid. A Selective Method for Converting the Carbonyl Group to Methylene” J. Org. Chem. 1973, 38, 2675-2681.
17.Doyle, M.P.; Zaleta M.A.; DeBoer J.E.; Wierenga W. “Reactions of the Nitrosonium Ion. V. Nitrosative Cleavage of the Carbon-Nitrogen Double Bond. The Attempted Exchange of Oxygen for Nitrogen” J. Org. Chem. 1973, 38, 1663-1667.
16.Doyle, M.P.; DeBruyn D.J.; Scholten D.J. “The Disproportionation of Trityl Alkyl Ethers. The Synthesis of Aldehydes and Ketones in a Cationic Chain Reaction Involving Hydride Transfer” J. Org. Chem. 1973, 38, 625-626.
15.Doyle, M.P.; Mungall W.S. “A New Approach to Organic Laboratory Projects” J. Chem. Educ. 1973, 50, 358.
14.Doyle, M.P.; Busman S.; Majiecko J. “The Reaction Between Azide and Nitronium Ions. The Formation and Decomposition of Nitryl Azide” J. Am. Chem. Soc. 1973, 95, 952-953.
13.Doyle, M.P.; DeBruyn D. J.; Kooistra D.A. “Silane Reductions in Acidic Media. I. Reduction of Aldehydes and Ketones in Alcoholic Media. A General Synthesis of Ethers” J. Am. Chem. Soc. 1972, 94, 3659-3661.
12.Doyle, M.P.; Wierenga W.; Zaleta, M.A. “Reactions of the Nitrosonium Ion. IV. Nitrosative Cleavage of the Carbon-Nitrogen Double Bond. The Reaction of N-Arylimines and Ketimines with Nitrosonium Salts” J. Org. Chem.1972, 37, 1597-1601.
11.Doyle, M.P.; Wierenga, W. “Reactions of the Nitrosonium Ion. III. Reaction of Alkyl Azides with Nitrosonium Compounds. The Effect of Solvent, Quenching Agent, and Nitrosonium Compound” J. Am. Chem. Soc. 1972, 94, 3901-3906.
10.Doyle, M.P.; Wierenga W. “Reactions of the Nitrosonium Ion. II. Reactions of Triphenylmethyl, Benzhydryl, and Benzyl Azides with Nitrosonium Compounds” J. Am. Chem. Soc. 1972, 94, 3896-3901.
9.Doyle, M.P.; Swedo R.J.; Rocek, J. “Pure Chromium(VI) Oxidations. The Effective Removal of Chromium(IV) from Interference in Oxidations by Chromic Acid” J. Am. Chem. Soc.1970, 92, 7599-7601.
8.Doyle, M.P.; Wierenga W. “Reactions of the Nitrosonium Ion. I. The Reaction of Alkyl Azides with Nitrosonium Salts. A New Method for the Production of Carbonium Ions” J. Am. Chem. Soc. 1970, 92, 4999-5001.
7.Trahanovsky, W.S.; Doyle, M.P.; Mullen, P.W.; Ong, C.C. “Preparation of Cycloheptanone via a Lewis-Acid Catalyzed Cyclization of 6-Heptenoyl Chloride to β-Chlorocycloheptanone” J. Org. Chem. 1969, 34, 3679-3681.
6.Trahanovsky, W.S.; Smyser, G.L.; Doyle M.P. “Acetolysis of 4-Bromobutyl-1-d2 p-Nitrobenzenesulfonate. Evidence for 1,4-Bromine Participation and the Existence of a 5-Membered Cyclic Bromonium Ion During Acetolysis” Tetrahedron Lett. 1968, 3127-3130.
5.Trahanovsky, W.S.; Doyle M.P. “Medium Effects, II. Cyclization of 6-Heptenyl p-Nitrobenenesulfonate During Solvolysis in 2,2,2-Trifluoroethanol” Tetrahedron Lett. 1968, 2155-2158.
4.Trahanovsky, W.S.; Doyle M.P. “Failure of the Principle of Hard and Soft Acids and Bases to Explain the Amount of Cyclization of Various 5-Hexenyl Derivatives During Acetolysis,” J. Chem. Soc., Chem. Commun. 1967, 1021-1022.
3.Trahanovsky, W.S.; Doyle M.P. “Medium Effects. I. Solvolysis of 5-Hexenyl p-Nitrobenzenesulfonate in Acetic Acid – Nonhydroxylic Solvent [20:80] Mixtures” J. Am. Chem. Soc. 1967, 89, 4867-4872.
2.Trahanovsky, W.S.; Doyle M.P.; Bartlett, P.D. “Nucleophilic Reactivity of the Carbon-Carbon Double Bond. VI. The Use of Urea as a Base in Acetolysis Reactions” J. Org. Chem. 1967, 32, 150-152.
1.Trahanovsky, W.S. and Doyle M.P. “Thermal Decomposition of t-Butylperoxy 6-bromohexanoate. Lack of Evidence for Radical Displacement on Carbon and 1,5-Bridged Bromine Radicals” J. Org. Chem. 1967, 32, 146-150.
  1. Doyle, M.P.; Protopopova, M.N. “Synthetic Opportunities of Diazocarbonyl Compounds: Highly Enantioselective Carbene Reactions Catalyzed by Chiral Dirhodium(II) Carboxamidates,” Proceedings of the Chiral ‘97 USA Symposium, Boston, MA, May 11-13, 1997, pg. 11-14.
  2. Doyle, M.P., “Highly Selective Catalytic Routes to Lactones,” Proceedings of the Chiral ‘95 USA Symposium, Boston, MA, May 15-16, 1995, pg. 59-62.
  3. Doyle, M.P., “Highly Enantioselective Syntheses with Dirhodium(II) Catalyst That Possess Chiral Ligands,” Proceedings of the Chiral ‘93 USA Symposium, Reston, VA, May 6-7, 1993, pg. 35-40.
  4. Doyle, M.P., “Organic Chemistry – The Beginning of Organized Understanding of Chemistry,” Proceedings of the Tenth International Conference on Chemical Education, University of Waterloo, Ontario, Canada, August 20-25, 1989; pg. 152-161.
Book Chapters
  1. Xu, X.; Trong, P.; Doyle, M.P. “Dirhodium-Catalysed Domino Reactions,” in Science of Synthesis: Applications of Domino Transformations in Organic Synthesis 1, Snyder, S. A., Ed., Georg Thieme Verlag KG, New York, 2016. Chapter 1.6.2; pg. 511-534.
  2. Sha, Q.; Deng, Y.; Doyle, M.P., “The Future of Catalysis by Chiral Lewis Acids,” in Topics in Organometallic Chemistry: Chiral Lewis Acids, Mikami, K., Ed., Springer International Publishing Switzerland, 2015, pp 1-25.
  3. Doyle, M.P.; Yu. L.; Ratnikov, M. O. “Catalytic, Asymmetric, Intramolecular Carbon-Hydrogen Insertion” in Organic Reactions, 2013, 80, 1-131.
  4. Timmons, D.; Doyle, M.P., “Chiral Dirhodium(II) Catalysts and their Applications,” in Metal Bonds Between Metal Atoms, Third Edition, F.A. Cotton, C. A. Murillo, and R. A.. Walton, Eds., Springer Science and Business Media, New York, 2005, Chapter 13.
  5. Doyle, M.P. “Chiral Dirhodium(II) Carboxamidates for Asymmetric Cyclopropanation and Carbon-Hydrogen Insertion Reactions,” in Modern Rhodium-Catalyzed Transformations, P. A. Evans, Ed., Wiley-VCH, New York, 2005.
  6. Doyle, M.P. “Metal Carbene Reactions from Dirhodium(II) Catalysts,” in Topics in Organometallic Chemistry Vol. 10, K.-H. Dötz, Ed., Springer-Verlag GmbH, Berlin, Germany, 2004, pg. 203-222.
  7. Doyle, M.P. “Chiral Dirhodium(II) Carboxamidates for Catalytic Asymmetric Synthesis,” in New Methodologies in Asymmetric Catalysis, S. Malhotra, Ed., Oxford University Press, Oxford, England, 2004.
  8. Doyle, M.P. “Synthetic Carbene and Nitrene Chemistry” in Contemporary Reactive Intermediate Chemistry, R. A. Moss, M. S. Platz, and M. Jones, Jr., Eds., John Wiley & Sons, Inc., New York, 2004.
  9. Doyle, M.P.; Forbes, D. C. “Catalytic Generation and Reactions of Oxygen and Nitrogen Ylides,” in Nitrogen, Oxygen, and Sulfur Ylide Chemistry, J. S. Clark, Ed., Oxford University Press, Oxford, 2002, Ch. 2.3, pg. 141-152.
  10. Doyle, M.P.; Ren, T. “The Influence of Ligands of Dirhodium(II) on Reactivity and Selectivity in Metal Carbene Reactions,” in Progress in Inorganic Chemistry, Vol. 49, K. Karlin, Ed., John Wiley & Sons, Inc., New York, 2001, pp. 113-168.
  11. Doyle, M.P. “Asymmetric Cyclopropanation and C-H Insertion,” in Catalytic Asymmetric Synthesis, Second Edition, I. Ojima, Ed., John Wiley & Sons, Inc., New York, 2000, Chapter 5.
  12. Doyle, M.P.; Forbes, D. C. “Catalytic Enantioselective Cyclopropanation, Carbon-Hydrogen Insertion, and Ylide Reactions,” in Chemistry for the 21st Century: Transition Metal Catalyzed Reactions, S. G. Davies and S. Murahashi, Eds., Blackwell Science Ltd., Oxford, UK, 1999, Chapter 14, pp. 289-301.
  13. Doyle, M.P. “Catalysis with Dirhodium(II) Complexes,” in Catalysis by Di- and Polynuclear Metal Cluster Complexes, R. D. Adams and F. A. Cotton, Eds., VCH Publishers, New York, 1998, Chapter 7.
  14. Doyle, M.P. “Metal Carbene Complexes in Organic Synthesis: Cyclopropanation,” in Comprehensive Organometallic Chemistry II, Volume 12, L. S. Hegedus, Ed., Pergamon Press, New York, 1995, Chapter 5.1.
  15. Doyle, M.P. “Metal Carbene Complexes in Organic Synthesis: Diazodecomposition – Insertion and Ylide Chemistry,” in Comprehensive Organometallic Chemistry II, Volume 12, L. S. Hegedus, Ed., Pergamon Press, New York, 1995, Chapter 5.2.
  16. Contributor (9 entries) to “Encyclopedia of Reagents for Organic Synthesis,” L. A. Paquette, Editor-in-Chief, Wiley, New York, 1996.
  17. Doyle, M.P. “Asymmetric Cyclopropanation,” in Catalytic Asymmetric Synthesis, I. Ojima, Ed., VCH Publishers, New York, 1993, Chapter 3, pp. 63-99.
  18. Doyle, M.P. “Chiral Rhodium(II) Carboxamides. Remarkably Effective Catalysts for Enantio-selective Metal Carbene Transformations,” in Selectivity in Catalysis, M. E. Davis and S. L. Suib, Ed., ACS Symposium Series 517, American Chemical Society, Washington, D.C., 1993, pp. 40-57.
  19. Doyle, M.P. “Academic Industrial Undergraduate Research Partnerships,” in Partnerships in Chemical Research and Education, J. E. McEvoy, Ed., ACS Monograph, American Chemical Society, Washington, D.C., 1992, pp. 16-27.
  20. Doyle, M.P.; High, K. G.; Nesloney, C. L. “Addition Reactions Catalyzed by Rhodium(II) Carboxylates,” in Catalysis of Organic Reactions, W. E. Pascoe, Ed., Marcel Dekker, Inc., New York, 1992, pp. 293-305.
  21. Doyle, M.P. “Electronic and Steric Control in Intramolecular Carbon-Hydrogen Insertion Reactions of Diazo Compounds Catalyzed by Rhodium(II) Carboxylates and Carboxamides,” in Homogenous Transition Metal Catalyzed Reactions, W. R. Moser and D. W. Slocum, Eds., Advances in Chemistry Series 230. American Chemical Society, Washington, D.C., 1992, pp. 443-461.
  22. Doyle, M.P. “Research as Undergraduate Education,” in Undergraduate Education in Chemistry and Physics, M. R. Rice, Ed., The College Center for Curricular Thought, University of Chicago, Chicago, IL, 1986, pp. 134-150.
  23. Doyle, M.P. “Selectivity of Carbenes Generated from Diazirines,” in Chemistry of Diazirines, M. T. H. Liu, Ed., CRC Press, Inc., Boca Raton, Fl, 1987, pp. 33-74.
  24. Doyle, M.P. “Catalytic Methods for the Synthesis of Cyclopropanes,” in Catalysis of Organic Reactions, R. L. Augustine, Ed., Marcel Dekker, Inc., New York, 1985, pp. 47-72.
  25. Cheng, Q.-Q.; Doyle, M.P. “The Selection of Catalysts for Metal Carbene Transformations” in Adv. Organometal. Chem., Vol. 66 Perez, P. J., Ed., Elsevier Limited. Oxford, United Kingdom, 2016. Chapter 1, pp. 1-31. (DOI: 10.1016/bs.adomc.2016.07.002)
  1. Moss, R.A.; Doyle, M.P., Editors, “Contemporary Carbene Chemistry,” John Wiley & Sons, Inc., New York, NY, 2014.
  2. Eliel, E.L.; Wilen, S.H.; Doyle, M.P., “Basic Organic Stereochemistry,” John Wiley & Sons, Inc., New York, NY, 2001.
  3. Doyle, M.P., Editor, “Academic Excellence: The Role of Research in the Physical Sciences at Undergraduate Institutions,” Research Corporation, Tucson, AZ, 2000.
  4. Doyle, M.P., McKervey, M.A.; Ye, T. “Modern Catalytic Methods for Organic Synthesis with Diazo Compounds,” John Wiley & Sons, Inc., New York, NY, 1998.
  5. Doyle, M.P., Editor, “Asymmetric Catalysis,” Vol. 2 in Advances in Catalytic Processes, JAI Press, Greenwich, CT, 1997.
  6. Doyle, M.P., Editor, “Asymmetric Chemical Transformations,” Vol. 1 in Advances in Catalytic Processes, JAI Press, Greenwich, CT, 1995.
  7. Doyle, M.P.; Mungall, W.S. “Experimental Organic Chemistry,” John Wiley and Sons, Inc., New York, N.Y., 1980. A one-year introductory laboratory manual for organic chemistry.
  8. Doyle, M.P.; Neckers, D.C. “Problem Solutions Manual,” John Wiley and Sons, Inc., New York, N.Y., 1977. A problem solution manual to accompany “Organic Chemistry.”
  9. Doyle, M.P.; Neckers, D.C. “Programmed Study Guide,” John Wiley and Sons, Inc., New York, N.Y., 1977. A Study Guide to accompany “Organic Chemistry.”
  10. Doyle, M.P.; Neckers, D.C. “Organic Chemistry,” John Wiley and Sons, Inc., New York, N.Y., 1977. A one-year introductory organic chemistry textbook.
  11. Doyle, M.P.; West, C.T. “Stereoselective Reductions,” Dowden, Hutchinson and Ross, Inc., Stroudsburg, Pa. A “Benchmark Papers in Organic Chemistry” volume; C. A. VanderWerf, series editor, December, 1976.
  1. “Chiral catalysts for enantioselective synthesis” WO 1991014672, Doyle, M. P., inventor. March 21, 1991. AU, CA, JP. European Patent Office (AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LU, NL, SE). 
    Abstract:A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes a two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation. 

  2. “Chiral catalysts for enantioselective synthesis” Australian Patent 199107705, Doyle, M. P., inventor. March 21, 1991. 
    Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes a two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation. 

  3. “Method of Enantioselective Cyclopropanation Using Chiral Catalysts” U.S. Patent 5,175,311, Doyle, M. P., inventor. 
    Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation. December 29, 1992 

  4. “Method of Enantioselectively Inserting a Carbene” U.S. Patent 5,296,595. 
    Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation. 
    Filed: September 24, 1992 
    Date of Patent: March 22, 1994 
    Assignee: Research Corporation Technologies 
    Inventor: Michael P. Doyle 

  5. “Silylcarbonylation of 1-Alkynes” U.S. Patent 5,302,737. 
    Abstract: This invention provides a process to regioselectively silylcarbonylate 1-alkynes and in predominantly the Z-isomer with substantial absence of hydrosilylation by-products. The process involves reacting a 1-alkyne with an organosilane and carbon monoxide in a solvent in the presence of a catalyst. The catalyst is a carboxylate salt of a metal such as rhodium, iridium or rhenium. 
    Type: Grant 
    Filed: December 23, 1992 
    Date of Patent: April 12, 1994 
    Assignee: Trinity University 
    Inventors: Michael P. Doyle, Michael S. Shanklin 

  6. “Method of Enantioselectively Catalyzing a Reaction”, U.S. Patent RE38947. Doyle, M. P., inventor. 
    Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation. 
    Type: Grant 
    Filed: February 14, 1996 
    Date of Patent: January 24, 2006 
    Assignee: Research Corporation Technologies, Inc. 
    Inventor: Michael P. Doyle 
    See also: 

  7. “Chiral Catalysts for Enantioselective Synthesis,” Canadian Patent CA2,077,542C, Doyle, M. P., inventor. 
    Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation. 

  8. “Chiral Catalysts for Enantioselective Synthesis,” European Patent EP0594608 (B1) (Austria, Belgium, France, Great Britain, Luxembourg, Switzerland), Doyle, M. P., inventor. Also “Catalyseurs chiraux pour syntheses enantioselectives”, EP0594608A1, Doyle, M. P., inventor. October 15, 1997. Family: US (3)EP (1)JP (1)CA (1)DE (2)WO (1) 
    Abstract: Chiral catalyst and methods of using this catalyst for enantioselective syntheses The chiral catalyst has a ring with two metal atoms which has four bridging ligands oriented radially to the core axis. Each of these ligands has two complexing atoms, each complexed with one of the metal atoms. At least one of the bridging ligands has a chiral center that is attached to one of the complexing atoms. Preferably, all four bridging ligands comprise a chiral center bonded to one of the complexing atoms. The catalyst of the present invention has been found useful for catalyzing carbenoid transformation reactions, such as cyclopropanation. 

  9. “Lewis Acid-Catalysis Using Chiral Metal Complexes”, Australian Patent AU2002226035, Doyle, M.P., inventor, with Hu, Wenhao and Phillips, Ian. June 13, 2002 

  10. “Efficient Aziridination of Olefins Catalyzed by Dirhodium Catalysts,” U.S. Patent 7,662,969. 
    Abstract: This invention relates to compositions and methods for achieving the efficient aziridination of organic molecules, especially olefins. More specifically, the invention is directed to a mild, selective, and efficient aziridination protocol that involves catalysis by a mixed-valent dirhodium(II,III) catalyst (Rh25+). Especially preferred sources for forming such mixed-valent dirhodium(II,III) catalyst (Rh25+) are dirhodium(II) carboxamidates, such as dirhodium(II) caprolactamate, and their derivatives and analogues. 
    Type: Grant 
    Filed: March 15, 2006 
    Date of Patent: February 16, 2010 
    Assignee: University of Maryland, College Park 
    Inventor: Michael P. Doyle 

  11. “Allylic Oxidations Catalyzed by Dirhodium Catalysts under Aqueous Conditions,” U. S. Patent 8,163,944 B2. Doyle, M. P., inventor. 
    Abstract: The present invention relates to compositions and methods for achieving the efficient allylic oxidation of organic molecules, especially olefins and steroids, under aqueous conditions. The invention concerns the use of dirhodium (II,II) “paddlewheel complexes, and in particular, dirhodium carboximate and tert-butyl hydroperoxide as catalysts for the reaction. The use of aqueous conditions is particularly advantageous in the allylic oxidation of 7-keto steroids, which could not be effectively oxidized using anhydrous methods, and in extending allylic oxidation to enamides and enol ethers. 
    Type: Grant 
    Filed: October 6, 2008 
    Date of Patent: April 24, 2012 
    Assignee: University of Maryland College Park 
    Inventors: Michael P. Doyle, Arthur J. Catino, Hojae Choi, Jason M. Nichols