Synthesis of the Optically Active Diaryl Selenoxides

Abstract

Optically active diaryl selenoxides have been prepared by either asymmetric oxidation of diaryl selenides or optical resolution of diastereomeric aryl p-(l-menthyloxycarbonyl)phenyl selenoxides. Ena. ntiomerically pure selenoxide has been synthesized for the first time by ester exchange of the diastereomerically pure 1-menthyl ester with sodium methylate. Diaryl selenoxides with bulky ortho substituents were found to be stable toward thermal racemization. Optical purity of the asymmetric diaryl selenoxides was found to be determined by HPLC using optically active column.