Preparation of optically active ortho-chloro-and ortho-bromophenyl sulfoxides

C Imboden, P Renaud

Index: Imboden, Christoph; Renaud, Philippe Tetrahedron Asymmetry, 1999 , vol. 10, # 6 p. 1051 - 1060

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Citation Number: 10

Abstract

The preparation of the diastereomerically pure menthyl (S)-2-chloro-and (S)-2-bromophenyl sulfinates by esterification of the corresponding sulfinic acids with (1R, 2S, 5R)-(−)-menthol and recrystallization/epimerization is reported. The two sulfinates have been converted into enantiomerically pure aryl, vinyl and alkyl sulfoxides by reaction with organomagnesium reagents. These sulfoxides are useful chiral auxiliaries to control the stereochemical ...