Development of a new carbon-carbon bond forming reaction. New organic chemistry of sulfur dioxide. Asymmetric four-component synthesis of polyfunctional sulfones

V Narkevitch, S Megevand, K Schenk…

Index: Narkevitch; Megevand; Schenk; Vogel Journal of Organic Chemistry, 2001 , vol. 66, # 15 p. 5080 - 5093

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Citation Number: 34

Abstract

At low temperature 1-alkoxy-1, 3-dienes add to sulfur dioxide activated by a Lewis or Brønstedt acid and generate zwitterionic intermediates that can be quenched by enoxysilanes. The resulting β, γ-unsaturated silyl sulfinates can be desilylated and reacted with methyl iodide to provide polyfunctional sulfones. Exploratory studies of this four- component synthesis of sulfones are reported. Enantiomerically pure derivatives ...