A new synthesis of enantiomerically pure n-alkyl 4-bromobenzenesulfinates and their configurational assignment

Article abstract of DOI:10.1016/0957-4166(95)00253-L

(S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol reacts with 4-bromobenzenesulfinyl chloride to give a single diastereomer of the corresponding sulfinamide in high yield. By an acidic alcoholysis of the sulfinamide with primary alcohols one obtains enantiomerically pure new (R)-(+)-n-alkyl 4-bromobenzenesulfinates. The configurations of the sulfinamide and the sulfinates derived from it have been determined by ¹H-NMR and molecular modeling.