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Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes

Brochu, Michael P. and Brown, Sean P. and MacMillan, David W. C. (2004) Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes. Journal of the American Chemical Society, 126 (13). pp. 4108-4109. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20170420-115316089

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Abstract

The first direct enantioselective catalytic α-chlorination of aldehydes has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective chlorination of aldehydes to generate α-chloro aldehydes, an important chiral synthon for chemical and medicinal agent synthesis. The use of imidazolidinone 3 as the asymmetric catalyst has been found to mediate the halogenation of a large variety of aldehyde substrates with the perchlorinated quinone 1 serving as the electrophilic chlorinating reagent. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. The capacity of catalyst 3 to override the inherent bias of resident stereogenicity in the chlorination of enantiopure β-chiral aldehydes is also described. Catalyst quantities of 5 mol % were generally employed in this study.


Item Type:Article
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http://dx.doi.org/10.1021/ja049562zDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja049562zPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja049562zPublisherSupporting Information
Additional Information:© 2004 American Chemical Society. Received 25 January 2004. Published online 11 March 2004. Published in print 1 April 2004. Financial support was provided by kind gifts from Bristol-Myers Squibb, Eli Lilly, and Merck Research Laboratories. D.W.C.M is grateful for support from the Sloan Foundation and Research Corporation. Teresa Beeson is thanked for additional enantioselectivity analysis.
Funders:
Funding AgencyGrant Number
Bristol-Myers SquibbUNSPECIFIED
Eli LillyUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
Alfred P. Sloan FoundationUNSPECIFIED
Research CorporationUNSPECIFIED
Record Number:CaltechAUTHORS:20170420-115316089
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20170420-115316089
Official Citation:Direct and Enantioselective Organocatalytic α-Chlorination of Aldehydes Michael P. Brochu, Sean P. Brown, and David W. C. MacMillan Journal of the American Chemical Society 2004 126 (13), 4108-4109 DOI: 10.1021/ja049562z
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76770
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:21 Apr 2017 13:53
Last Modified:21 Apr 2017 13:53

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