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

Article abstract of DOI:10.1016/S0040-4020(01)87253-7

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 α-keto esters and α-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.