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The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes

Paras, Nick A. and MacMillan, David W. C. (2002) The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes. Journal of the American Chemical Society, 124 (27). pp. 7894-7895. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170414-104130125

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Abstract

The first enantioselective organocatalytic alkylation of electron-rich benzene rings with α,β-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective construction of benzylic stereogenicity, an important chiral synthon for natural product and medicinal agent synthesis. The (2S,5S)-5-benzyl-2-tert-butylimidazolidinone amine catalyst has been found to mediate the conjugate addition of a wide variety of substituted and unsubstituted anilines to unsaturated aldehydes. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 10 mol % were generally employed in this study, successful alkylations conducted with catalyst loadings as low as 1 mol % are described.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja025981pDOIArticle
http://pubs.acs.org/doi/abs/10.1021%2Fja025981pPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja025981pPublisherSupporting Information
Additional Information:© 2002 American Chemical Society. Received 20 February 2002. Published online 12 June 2002. Published in print 1 July 2002. Financial support was provided by AstraZeneca, GlaxoSmithKline, Johnson and Johnson, Materia, Merck Research Laboratories, Research Corporation (Cottrell Scholarship) and Roche Biosciences. We also thank Great Lakes for their generous donation of amino acids.
Funders:
Funding AgencyGrant Number
AstraZenecaUNSPECIFIED
GlaxoSmithKlineUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
MateriaUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
Cottrell Scholar of Research CorporationUNSPECIFIED
Roche BiosciencesUNSPECIFIED
Issue or Number:27
Record Number:CaltechAUTHORS:20170414-104130125
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170414-104130125
Official Citation:The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes Nick A. Paras and David W. C. MacMillan Journal of the American Chemical Society 2002 124 (27), 7894-7895 DOI: 10.1021/ja025981p
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76570
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:14 Apr 2017 18:04
Last Modified:03 Oct 2019 17:02

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