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New Strategies for Organic Catalysis: The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition

Jen, Wendy S. and Wiener, John J. M. and MacMillan, David W. C. (2000) New Strategies for Organic Catalysis: The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition. Journal of the American Chemical Society, 122 (40). pp. 9874-9875. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20170406-070216339

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Abstract

Our laboratory has been engaged in the design of broadly useful new strategies for enantioselective catalysis that utilize organic chemicals as reaction catalysts. In our recent study, we reported that the LUMO-lowering activation of α,β-unsaturated aldehydes using the reversible formation of iminium ions with chiral imidazolidinones 1 (eq 1) is a valuable platform for the development of enantioselective organocatalytic Diels−Alder reactions (eq 2). In this work, we reveal that this catalytic strategy is also amenable to [3 + 2] cycloadditions between nitrones and α,β-unsaturated aldehydes to provide isoxazolidines (eq 3), useful synthons for the construction of biologically important amino acids, β-lactams, amino carbohydrates, and alkaloids. To our knowledge, this is the first example of an organocatalytic 1,3-dipolar cycloaddition. Moreover, this study further documents that chiral amines can be employed as asymmetric catalysts for a range of transformations that traditionally utilize metal salts.


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http://dx.doi.org/10.1021/ja005517pDOIArticle
http://pubs.acs.org/doi/full/10.1021/ja005517pPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja005517pPublisherSupporting Information
Additional Information:© 2000 American Chemical Society. Received 8 August 2000. Published online 26 September 2000. Published in print 1 October 2000. W.S.J. and J.J.M.W. are grateful for predoctoral NSF fellowships. This research has been supported by kind gifts from Merck, Roche-Biosciences, and Warner-Lambert.
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NSF Predoctoral FellowshipUNSPECIFIED
Record Number:CaltechAUTHORS:20170406-070216339
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20170406-070216339
Official Citation:New Strategies for Organic Catalysis:  The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition Wendy S. Jen, John J. M. Wiener, and David W. C. MacMillan Journal of the American Chemical Society 2000 122 (40), 9874-9875 DOI: 10.1021/ja005517p
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ID Code:75769
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:06 Apr 2017 17:02
Last Modified:06 Apr 2017 17:02

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