Asymmetric Trans-Addition Reactions Using Chiral Selenobinaphthyls

Asymmetric trans-addition reactions of (E)-phenylpropene, a mechanistically novel reactions, have been achieved by using chiral selenium-containing binaphthyl derivatives. Introduction of an amide group at 2′-position in the binaphthyl skeleton enhances considerably the diastereomeric excess (d.e.) of the asymmetric reaction presumably due to attractive interaction between the nitrogen lone pair and the seleniranium intermediate. Introduction of another chiral center in the amide group further enhances the d.e. as high as 79 %, which is the highest asymmetric induction ever achieved in the asymmetric trans-addition reaction.