SN2′ addition/1,2-elimination of dimethylsulfonium methylide with epoxy vinyl sulfones: synthesis of exocyclic cross-conjugated dienyl sulfones

Vikas Sikervar; Philip L. Fuchs

doi:10.1039/C0CC05405D

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S_N2′ addition/1,2-elimination of dimethylsulfonium methylide with epoxy vinyl sulfones: synthesis of exocyclic cross-conjugated dienyl sulfones†

Vikas Sikervar^a and Philip L. Fuchs*^a

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* Corresponding authors

^a Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA
E-mail: pfuchs@purdue.edu
Fax: +1765-494-0239
Tel: +1765-494-5242

Abstract

Dimethylsulfonium methylide undergoes S_N2′ addition/1,2-elimination with epoxy vinyl sulfones to generate enantiopure six and seven membered cross-conjugated hydroxy vinyl sulfones. Moderate to excellent yields were obtained for both six and seven membered substrates.

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Article information

DOI: https://doi.org/10.1039/C0CC05405D
Article type: Communication
Submitted: 06 Dec 2010
Accepted: 17 Jan 2011
First published: 09 Feb 2011

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Chem. Commun., 2011,47, 3472-3474

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S_N2′ addition/1,2-elimination of dimethylsulfonium methylide with epoxy vinyl sulfones: synthesis of exocyclic cross-conjugated dienyl sulfones

V. Sikervar and P. L. Fuchs, Chem. Commun., 2011, 47, 3472 DOI: 10.1039/C0CC05405D

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