Tetrahedron

Nad (p) h models-xvii1: Metal ion catalyzed reduction of imines by 3, 5-diethoxycarbonyl 2, 6-dimethyl-1, 4-dihydropyridine (hantzsch ester)

JB Steevens, UK Pandit

Index: Steevens, J. B.; Pandit, U. K. Tetrahedron, 1983 , vol. 39, # 8 p. 1395 - 1400

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Citation Number: 38

Abstract

The reduction of imines by 3, 5-diethoxycarbonyl-2, 6-dimethyl-1, 4-dihydropyridine, an NAD (P) H model, is catalyzed by Mg2+ ions. Kinetic measurements of the reduction of a series of imines derived from substituted benzaldehydes, show a very small polar substituent effect (θ=− 0.39). The results have been interpreted in terms of a mechanism involving a hydride transfer from the dihydropyridine derivative to an imine-Mg2+ ion complex.