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

Jirí Pospísil, Tomá Pospísil and István E. Markó*

*Université Catholique de Louvain, Département de Chimie, Bâtiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium, Email: markochim.ucl.ac.be

J. Pospisil, T. Pospisil, I. E. Marko, Org. Lett., 2005, 7, 2373-2376.

DOI: 10.1021/ol050649e

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Abstract

A modification of the classical Julia-Lythgoe olefination using sulfoxides instead of sulfones affords 1,2-di-, tri-, and tetrasubstituted olefins in moderate to excellent yields and E/Z selectivity. The mild conditions involve in situ benzoylation and SmI₂/HMPA-mediated reductive elimination as key steps.

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Key Words

Julia olefination, Samarium Diiodide, Sulfoxides, Alkenes

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ID: J54-Y2005-600