Michael J. Krische

mkrische@mail.utexas.edu
Organic Chemistry
Professor, Faculty
Environmental Science Institute
Robert A. Welch Chair in Science
Director, Center for Green Chemistry and Catalysis
Michael J. Krische

Contact Information

Office
WEL 5.146
Office Phone
232-5892
Fax
471-8696

Research Group

The Krische Group

Education

BS, University of California at Berkeley (1989);   Fulbright Fellowship, Helsinki University (1990);   PhD, Stanford University (1996); Postdoctoral Studies, Universite' Louis Pasteur (1999)

Awards

Novartis Chemistry Lectureship (2008);   Dowpharma Prize (2007);   Elias J. Corey Award (2007);   Presidential Green Chemistry Award (2007);   Solvias Ligand Prize (2006);   Japanese Society of Synthetic Chemistry, Lectureship on Organic Synthesis (2005);   Johnson & Johnson Focused Giving Award (2005);   Alfred P. Sloan Research Fellowship (2003);   Camille Dreyfus Teacher Scholar Award (2003);   Lilly Grantee Award (2002);   Frasch Foundation Award in Chemistry (2002);   Cottrell Scholar Award (2002);   National Science Foundation-CAREER Award (2000);   NIH Post-Doctoral Fellow (1997);   Peter Veatch Fellow (1995);   Fulbright Fellow (1990);   Sigma Xi Fellow (1990);   President's Undergraduate Fellow (1989)

Natural Product Synthesis, Catalytic Reaction Development, Organometallic Chemistry and Self-Assembly

Research in the Krische group focuses on catalytic reaction development with attendant applications in natural product synthesis. A central theme involves the identification of new reactivity patterns, the evolution of related catalytic processes and, ultimately, the development of new synthetic strategies. Specific areas of research include: (a) hydrogen-mediated C-C bond formation, (b) nucleophilic catalysis via phosphine conjugate addition, (c) catalytic tandem conjugate addition-electrophilic trapping, and (d) metal-catalyzed [2+2]cycloaddition.

H2-Mediated C-C Bond Formation: Alkene hydroformylation is the largest volume application of homogeneous metal catalysis and the prototypical example of hydrogen-mediated C-C bond formation. Remarkably, while hydroformylation is practiced on vast scale, systematic efforts toward the development of hydrogenative C-C couplings that extend beyond carbon monoxide coupling have remained absent from the literature. Ideally, it would be desirable to couple two or more organic molecules simply through their exposure to gaseous hydrogen in the presence of a metal catalyst. This goal represents the primary focus of research in our laboratory.



Representative Publications

  • Barchuk, A.; Ngai, M.-Y.; Krische, M. J.  "Enantioselective Iridium Catalyzed Imine Vinylation: Optically Enriched Allylic Amines via Alkyne-Imine Reductive Coupling Mediated by Hydrogen" J. Am. Chem. Soc. 129 (2007): 12644.

  • Skucas, E.; Kong, J.-R.; Krische, M. J.  "Enantioselective Reductive Coupling of Acetylene to N-Arylsulfonyl Imines via Rhodium Catalyzed C-C Bond Forming Hydrogenation: (Z)-Dienyl Allylic Amines" J. Am. Chem. Soc. 129 (2007): 7242.

  • "Highly Enantioselective Direct Reductive Coupling of Conjugated Alkynes and a-Ketoesters via Rhodium Catalyzed Asymmetric Hydrogenation" J. Am. Chem. Soc. 128 (2006): 718.

  • "Enantioselective Reductive Cyclization of 1,6-Enynes via Rhodium Catalyzed Asymmetric Hydrogenation: C-C Bond Formation Precedes Hydrogen Activation" J. Am. Chem. Soc. 127 (2005): 6174.

  • "Phosphine Catalyzed a-Arylation of Enones Using Hypervalent Bismuth Reagents: Regiospecific Enolate Arylation via Nucleophilic Catalysis" J. Am. Chem. Soc. 126 (2004): 5350.

  • "Catalytic Enone Allylation via Concomitant Activation of Latent Nucleophilic and Electrophilic Partners: Merging Organic and Transition Metal Catalysis" J. Am. Chem. Soc. 125 (2003): 7758.