Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Asymmetric Reduction with C1- and C2-Symmetric NADH Model Compounds Containing Chiral 1,1′-Binaphthyls
Masaki AmanoMotoshi WatanabeNaomichi BabaJun’ichi OdaYuzo Inouye
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1983 Volume 56 Issue 12 Pages 3672-3678

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Abstract

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.

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