One-Pot, Three-Component Synthesis of Open-Chain, Polyfunctional Sulfones

Laure Bouchez; Pierre Vogel

doi:10.1055/s-2002-19797

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Synthesis 2002(2): 0225-0231
DOI: 10.1055/s-2002-19797

PAPER

One-Pot, Three-Component Synthesis of Open-Chain, Polyfunctional Sulfones

Laure Bouchez, Pierre Vogel*
Institut de chimie moléculaire et biologique de l’Ecole Polytechnique Fédérle de Lausanne, Switzerland
Fax: +41(21)6939375; e-Mail: pierre.vogel@epfl.ch;

Further Information

Publication History

Received 6 September 2001
Publication Date:
03 August 2004 (online)

Abstract
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Abstract

Silyl enol ethers of esters, ketones, as well as allylstannane and allylsilanes react with sulfur dioxide activated with t-BuMe₂SiOSO₂CF₃ to give silyl sulfinates that can be reacted in the same pot with a variety of electrophiles generating the corresponding polyfunctional sulfones. The silyl sulfinate intermediates are formed via ene-reactions following probably concerted mechanisms.

Keywords

ene-reaction - enoxysilanes - sulfinates - sulfones

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To our knowledge the ene-reaction of sulfur dioxide with silyl enol ether derived from ketone had never been reported.