Enantioselective reduction of C=O and C=N compounds with NADH model N,N,1,2,4-pentamethyl-1,4-dihydronicotinamide

J.P.G. Versleijen, M.S.T.H. Sanders-Hovens, S.A.M. Vanhommerig, J.A.J.M. Vekemans, E.M. Meijer

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24 Citations (Scopus)

Abstract

The scope and mechanism of enantioselective hydride transfer from NADH model 4 to prochiral C=O and C=N compounds were investigated. Efficient chirality transfer from 4 to a-keto esters and a-methoxycarbonylimino esters was achieved. The resemblance in reactivity and stereochemistry of the prochiral C=O and C=N-CO2Me functionalities in the hydride transfer reaction is attributed to the intervention of a similar Mg(ClO4)2-mediated ternary complex.
Original languageEnglish
Pages (from-to)7793-7802
Number of pages10
JournalTetrahedron
Volume49
Issue number35
DOIs
Publication statusPublished - 1993

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