Publications

Journal Publications

Proceedings

  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)
Books
  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.
Patents
  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: https://www.finnegan.com/en/tools/in-re-michael-doyle/analysis.html 

  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 

Publications

Proceedings
  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)
Books
  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.
Patents
  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: https://www.finnegan.com/en/tools/in-re-michael-doyle/analysis.html 

  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 

Publications

Proceedings
  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)
Books
  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.
Patents
  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: https://www.finnegan.com/en/tools/in-re-michael-doyle/analysis.html 

  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