Abstract

The stereoselectivities of organic reactions will be investigated theoretically in order to develop reliable qualitative and quantitative techniques to predict stereoselectivities and to design useful new reagents and catalysts. The success of this work should facilitate the efficient synthesis of pharmaceutical agents and will eventually help elucidate the origins of enzyme stereospecificity. In previous years of support, we have developed empirical transition state models based upon quantum mechanical transition structure calculations, and we have shown how these can be used to understand rates and selectivities of many types of organic reactions. This proposal describes the progress which has been made and summarizes the state of the art in modeling stereoselectivities of organic reactions.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
2R01GM036700-08
Application #
3291158
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1986-02-01
Project End
1997-01-31
Budget Start
1993-02-01
Budget End
1994-01-31
Support Year
8
Fiscal Year
1993
Total Cost
Indirect Cost

  Institution

Name
University of California Los Angeles
Department
Type
Schools of Arts and Sciences
DUNS #
119132785
City
Los Angeles
State
CA
Country
United States
Zip Code
90095

  Publications

Lam, Yu-Hong; Grayson, Matthew N; Holland, Mareike C et al. (2016) Theory and Modeling of Asymmetric Catalytic Reactions. Acc Chem Res 49:750-62
Hie, Liana; Fine Nathel, Noah F; Hong, Xin et al. (2016) Nickel-Catalyzed Activation of Acyl C-O Bonds of Methyl Esters. Angew Chem Int Ed Engl 55:2810-4
Phillips, Eric M; Mesganaw, Tehetena; Patel, Ashay et al. (2015) Synthesis of ent-ketorfanol via a C-H alkenylation/torquoselective 6? electrocyclization cascade. Angew Chem Int Ed Engl 54:12044-8
Pham, Hung V; Karns, Alexander S; Vanderwal, Christopher D et al. (2015) Computational and experimental investigations of the formal dyotropic rearrangements of Himbert arene/allene cycloadducts. J Am Chem Soc 137:6956-64
Krenske, Elizabeth H; Houk, K N; Harmata, Michael (2015) Computational analysis of the stereochemical outcome in the imidazolidinone-catalyzed enantioselective (4 + 3)-cycloaddition reaction. J Org Chem 80:744-50
Hooper, Joel F; James, Natalie C; Bozkurt, Esra et al. (2015) Medium-Ring Effects on the Endo/Exo Selectivity of the Organocatalytic Intramolecular Diels-Alder Reaction. J Org Chem 80:12058-75
Hie, Liana; Fine Nathel, Noah F; Shah, Tejas K et al. (2015) Conversion of amides to esters by the nickel-catalysed activation of amide C-N bonds. Nature 524:79-83
Lam, Yu-Hong; Houk, K N (2015) Origins of stereoselectivity in intramolecular aldol reactions catalyzed by cinchona amines. J Am Chem Soc 137:2116-27
Patel, Ashay; Vella, Joseph R; Ma, Zhi-Xiong et al. (2015) Transition State Gauche Effects Control the Torquoselectivities of the Electrocyclizations of Chiral 1-Azatrienes. J Org Chem 80:11888-94
Noey, Elizabeth L; Tibrewal, Nidhi; Jiménez-Osés, Gonzalo et al. (2015) Origins of stereoselectivity in evolved ketoreductases. Proc Natl Acad Sci U S A 112:E7065-72

Showing the most recent 10 out of 113 publications