Asymmetric Reduction with C1- and C2-Symmetric NADH Model Cpmpounds Containing Chiral 1,1'-Binaphthyls

Article abstract of DOI:10.1246/bcsj.56.3672

The present study deals with Mg-catalyzed asymmetric reduction of ethyl benzoylformate by the use of C₂-symmetric NADH model compounds in which axial dissymmetry(chiral 1,1'-binaphthyl derivatives) was introduced as a chiral source for the first time and the results were compared with those obtained by the corresponding C₁-symmetric models bearing the same chiral center.Better e.e.'s of the reduction product were obtained by the use of NADH models having C₂-symmetry than does the corresponding C₁-symmetric ones.Further, the kind of bonding as well as the distance between chiral binaphthyl and the reaction center affected the stereochemical course of hydrogen transfer.