ORGANOSULPHUR COMPOUNDS-LXIX OPTICALLY ACTIVE SULPHINATES: A NEW TYPE OF ENANTIOSELECTIVE ASYMMETRIC SYNTHESIS AND KINETIC RESOLUTION

Article abstract of DOI:10.1016/S0040-4020(01)86031-2

Optically active sulphinates with the sulphur atom as a sole centre of chirality are prepared by two methods.The first involves the reaction of symmetrical sulphites with tert-butylmagnesium chloride in the presence of optically active aminoalcohols.This new asymmetric, enantioselective synthesis affords t-butylsulphinates with 40-70percent enantiomeric excess values.The second approach is based on a new type of kinetic resolution taking place when racemic sulphinates are reacted with tert-butylmagnesium chloride complexed by optically active alkaloid bases.Both the recovered sulphinates and sulphoxides formed in this reaction show moderate optical purities.