An Efficient and Practical Route to Enantiomerically Pure (+)-(1R,2R)- and (-)-(1S,2S)-1,2-Diphenylethane-1,2-diamines

Abstract

The synthesis of the title compounds is easily achieved by the asymmetric Sharpless dihydroxylation of trans-stilbene to the corresponding enantiomerically pure diols. The conversion of the diols to the di-p-toluenesulfonates and subsequent reaction with sodium azide affords the diazides, which are reduced by lithium aluminum hydride to the optically pure 1,2-diamines.