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Letter

Sulfoxides in Julia−Lythgoe Olefination: Efficient and Stereoselective Preparation of Di-, Tri-, and Tetrasubstituted Olefins

Supporting Info

Jirí Pospíšil, Tomáš Pospíšil, and István E. Markó*

Universit Catholique de Louvain, Dpartement de Chimie, Btiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium

Org. Lett., 2005, 7 (12), pp 2373–2376

DOI: 10.1021/ol050649e

Publication Date (Web): May 19, 2005

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

, marko@chim.ucl.ac.be

Abstract

A novel modification of the classical Julia−Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and SmI₂/HMPA- or DMPU-mediated reductive elimination, 1,2-di-, tri-, and tetrasubstituted olefins in moderate to excellent yields and E/Z selectivity. The conditions are mild, and the procedure is broadly applicable.

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History

Published In Issue June 09, 2005
Received March 26, 2005

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Letter

Sulfoxides in Julia−Lythgoe Olefination: Efficient and Stereoselective Preparation of Di-, Tri-, and Tetrasubstituted Olefins