A symmetric oxyselenenylation of simple olefins using optically active selenobinaphthyls

Asymmetric 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.