A symmetric oxyselenenylation of simple olefins using optically active selenobinaphthyls

Abstract

AbstractAsymmetric trans‐addition reactions of simple olefins have been performed by using optically active 2‐selenobinaphthyls 1,2a–g. Introduction of an amide group at the 2′‐position in the binaphthyl skeleton enhances considerably the diastereomeric excess (de) of the asymmetric methoxyselenenylation. In the case of trans‐olefins, introduction of another chiral center in the amide group further enhances the de due to double stereodifferentiation between the (R)‐binaphthyl skeleton and the chiral amide group introduced at the 2′‐position in the binaphthyl skeleton. The use of chiral nucleophiles is also effective to enhance the de for symmetrical cis‐olefins.