A Recyclable Fluorous (S)-Pyrrolidine Sulfonamide Promoted Direct, Highly Enantioselective Michael Addition of Ketones and Aldehydes to Nitroolefins in Water

Liansuo Zu, Jian Wang, Hao Li, and Wei Wang*
Department of Chemistry, University of New Mexico, Albuquerque, New Mexico 87131-0001
Org. Lett., 2006, 8 (14), pp 3077–3079
DOI: 10.1021/ol061053+
Publication Date (Web): June 6, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, wwang@unm.edu

Abstract

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A recycle and reusable fluorous (S)-pyrrolidine sulfonamide organocatalyst has been developed for promoting highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water. The organocatalyst is conveniently recovered from the reaction mixtures by fluorous solid-phase extraction and can be subsequently reused (up to six cycles) without a significant loss of catalytic activity and stereoselectivity.

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History

  • Published In Issue July 06, 2006
  • Received May 1, 2006

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