Michael J. Krische

mkrische@mail.utexas.edu

Professor, Faculty
Environmental Science Institute
Director, Center for Green Chemistry and Catalysis
Robert A. Welch Chair in Science

Research Group

The Krische Group

Education

BS, University of California Berkley, 1989
Fulbright Fellowship, Helsinki University, 1990
PhD, Stanford University, 1996

Postdoctoral Studies, Universite' Louis Pasteur 1999

Awards

ACS Cope Scholar Award, 2013

GlaxoSmithKline Scholar Award, 2011

Mukaiyama Award, 2010
Humboldt Research Award, 2009
Tetrahedron Young Investigator Award, 2009
Novartis Lectureship Award, 2008
Presidential Green Chemistry Award, 2007
Dowpharma Prize, 2007
Elias J. Corey Award, 2007
Solvias Ligand Prize, 2006
Johnson & Johnson Focused Giving Award, 2005
Japanese Society of Synthetic Chemistry, Lectureship on Organic Synthesis, 2005
Camille Dreyfus Teacher Scholar Award, 2003
Alfred P. Sloan Research Fellowship, 2003
Cottrell Scholar Award, 2002
Lilly Grantee Award, 2002
Frasch Foundation Award in Chemistry, 2002
National Science Foundation-CAREER Award, 2000
NIH Post-Doctoral Fellow, 1997
Peter Veatch Fellow, 1995
Sigma Xi Fellow, 1990
Fulbright Fellow, 1990
Presidents Undergraduate Fellow, 1989

Affiliations

Center for Nano- and Molecular Science and Technology; Environmental Science Institute; Texas Materials Institute

Natural Product Synthesis, Catalytic Reaction Development, Organometallic Chemistry

Our research focuses on the development of byproduct-free catalytic C-C bond forming reactions of abundant, renewable feedstocks. A central theme involves the identification of new reactivity patterns, the evolution of related catalytic processes and, ultimately, the development of new strategies for the synthesis of natural products or commodity chemicals.

 

One major area of research involves the development of C-C bond forming hydrogenations and transfer hydrogenations. We have found that diverse π-unsaturated reactants reductively couple to carbonyl compounds and imines under hydrogenation conditions, providing a byproduct-free alternative to stoichiometric organometallic reagents in a range of C=X (X = O, NR) addition processes. This concept is extended further by “C-C bond forming transfer hydrogenations”. Here, alcohol dehydrogenation triggers hydrometallation of π-unsaturated reactants to generate transient organometallics, enabling byproduct-free aldehyde addition directly from the alcohol oxidation level. This body of work represents the first C-C bond forming hydrogenations beyond hydroformylation, and evokes the question of whether all processes employing stoichiometric organometallic reagents can be conducted catalytically under hydrogenation conditions.

Representative Publications

Lu, Y.; Woo, S. K.; Krische, M. J. “Total Synthesis of Bryostatin 7 via C-C Bond Forming Hydrogenation,” J. Am. Chem. Soc. 132 (2011): 13876.

Zhang, Y. J.; Yang, J. H.; Kim, S. H.; Krische, M. J. “anti-Diastereo- and Enantioselective Carbonyl (Hydroxymethyl)allylation from the Alcohol or Aldehyde Oxidation Level: Allyl Carbonates as Allylmetal Surrogates,” J. Am. Chem. Soc. 132 (2010): 4562.

Kim, I. S.; Ngai, M.-Y.; Krische, M. J. "Enantioselective Iridium Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate," J. Am. Chem. Soc. 130 (2008): 6340.

Bee, C.; Han, S. B.; Hassan, A.; Iida, H.; Krische, M. J. "Diastereo- and Enantioselective Hydrogenative Aldol Coupling of Vinyl Ketones: Design of Effective Monodentate TADDOL-Like Phosphonite Ligands," J. Am. Chem. Soc 130 (2008): 2747.

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.