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Mathematical description of kinetic resolution with an enantiomerically impure catalyst and nonracemic substrate

Ismagilov, Rustem F. (1998) Mathematical description of kinetic resolution with an enantiomerically impure catalyst and nonracemic substrate. Journal of Organic Chemistry, 63 (11). pp. 3772-3774. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20130821-160719423

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Abstract

Kinetic resolution is an important method in organic chemistry; catalytic kinetic resolution is especially attractive because a smaller amount of the optically active material is required. In principle, a naturally occurring catalyst (enzyme) or a synthetic catalyst can be employed. Possible disadvantages of an enzymatic catalyst include limited scope of reactions and substrates; therefore, there is an increasing effort targeted at the design of chemical catalysts for kinetic resolution. The most useful parameter in comparing different catalysts is the selectivity factor S, which is the ratio of the rate constants for the reaction of the catalyst with the two enantiomers of the substrate (S = (k_1/k_2), see below). Mathematical treatment of kinetic resolution should provide a way to calculate S from experimental observables, and for enantiomerically pure catalysts the equations are well-known from the work of Kagan and others.


Item Type:Article
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http://dx.doi.org/10.1021/jo972299iDOIArticle
http://pubs.acs.org/doi/full/10.1021/jo972299i?PublisherArticle
ORCID:
AuthorORCID
Ismagilov, Rustem F.0000-0002-3680-4399
Additional Information:Copyright © 1998 American Chemical Society. Published In Issue: May 29, 1998. Received December 22, 1997. I thank Olafs Daugulis, Dr. Igor Alabugin, Prof. Edwin Vedejs, and Prof. Stephen Nelsen for helpful discussions and encouragement. A fellowship from Dow Chemical is gratefully acknowledged.
Funders:
Funding AgencyGrant Number
Dow Chemical CompanyUNSPECIFIED
Subject Keywords:asymmetric catalysis
Record Number:CaltechAUTHORS:20130821-160719423
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20130821-160719423
Official Citation:Mathematical Description of Kinetic Resolution with an Enantiomerically Impure Catalyst and Nonracemic Substrate Rustem F. Ismagilov The Journal of Organic Chemistry 1998 63 (11), 3772-3774
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:40797
Collection:CaltechAUTHORS
Deposited By: Whitney Barlow
Deposited On:23 Aug 2013 21:26
Last Modified:23 Mar 2015 22:15

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