β-Disulfoxides. II. The Preparation of Some Optically Active β-Disulfoxides

Abstract α-Sulfinylcarbanions (1) derived from methyl-substituted sulfoxides readily react with arenesulfinic esters (2) to give the corresponding β-disulfoxides (3) in good yields. The reaction was conducted using (−)-menthyl (−)-(S)-benzenesulfinate ((−)-(S)-2b), (−)-menthyl (−)-(S)-p-toluenesulfinate ((−)-(S)-2c), and α-p-tolylsulfinylcarbanion derived from (+)-(R)- or (−)-(S)-methyl p-tolyl sulfoxide to produce (R,S)- and/or (S,S)-diastereoisomers of five β-disulfoxides (3a–e). The configurational assignment for the diastereoisomers obtained was accomplished by a combination of NMR and polarimetric analyses.