Synlett 2008(4): 517-520  
DOI: 10.1055/s-2008-1032080
LETTER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Vinylcyclopropanes from Dienes and Sulfur Ylides

Raphaël Robiette*, Jacqueline Marchand-Brynaert
Université Catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve, Belgium
Fax: +32(10)474168; e-Mail: raphael.robiette@uclouvain.be;
Further Information

Publication History

Received 16 November 2007
Publication Date:
12 February 2008 (online)

Abstract

The reaction of aryl- and vinyl-stabilized sulfonium ylides with electron-poor dienes has been investigated. Clean cyclopropanation to 2-aryl- and 2-vinyl-substituted vinylcyclopropanes, with high regio- and stereocontrol, was observed. This new diastereoselective strategy was applied to formal synthesis of lamoxirene and dictyopterene B.