Chapter 5 The chemistry of α,β-unsaturated sulfoxides

Abstract

Publisher Summary This chapter is concerned with the use of α, β-unsaturated sulfoxides in organic synthesis and covers the chemistry of vinyl (alkenyl) and dienyl sulfoxides. Particular emphasis is given to the use of nonracemic α, β-unsaturated sulfoxides throughout, reflecting recent developments in this field. The chapter discusses the preparation of optically active α, β-unsaturated sulfoxides, electrophilic additions, nucleophilic additions to α, β-unsaturated sulfoxides. The chapter also discusses pericyclic reactions and rearrangements (such as additive Pummerer rearrangement, [2,3]-sigmatropic rearrangements, [3,3]-sigmatropic rearrangements ) of α, and β-unsaturated sulfoxides. The methods available for the synthesis of enantiomerically pure sulfoxides will result in their increasing importance in asymmetric synthesis as a result of the unique character of the sulfoxide functional group and its ability to exert a strong stereo-controlling influence.