Design of Sulfides with a Locked Conformation as Promoters of Catalytic and Asymmetric Sulfonium Ylide Epoxidation

Marion Davoust, Jean-François Brière, Paul-Alain Jaffrès, and Patrick Metzner*
Laboratoire de Chimie Molculaire et Thio-organique (UMR CNRS 6507), ENSICaen-Universit de Caen, 6 Boulevard du Marchal Juin, 14050 Caen, France patrick.metzner@ensicaen.fr
J. Org. Chem., 2005, 70 (10), pp 4166–4169
DOI: 10.1021/jo0479260
Publication Date (Web): April 9, 2005
Copyright © 2005 American Chemical Society
*

 To whom correspondence should be addressed. Tel:  Int. code +3323145-2885. Fax:  Int. code +3323145-2865.

Abstract

Abstract Image

A new generation of 2,5-dimethylthiolanes with a locked conformation was developed to promote the asymmetric addition of chiral sulfonium ylides to aldehydes. The novel chiral sulfur derivative 4 succeeded the synthesis of trans-stilbene oxide derivatives with enantiomeric ratios ranging from 95:5 to 98:2. This user-friendly organocatalytic process proved to be efficient with 20−10% of sulfide 4 in 1 or 2 days of reaction. An insight into the ylide intermediate conformation is given on the basis of a computational ab initio study.

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History

  • Published In Issue May 13, 2005
  • Received November 23, 2004

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