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

doi:10.1016/S0040-4020(01)87253-7

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

Macromolecular and Organic Chemistry

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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 language	English
Pages (from-to)	7793-7802
Number of pages	10
Journal	Tetrahedron
Volume	49
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4020(01)87253-7
Publication status	Published - 1993

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

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.",

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

year = "1993",

doi = "10.1016/S0040-4020(01)87253-7",

language = "English",

volume = "49",

pages = "7793--7802",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "35",

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TY - JOUR

T1 - Enantioselective reduction of C=O and C=N compounds with NADH model N,N,1,2,4-pentamethyl-1,4-dihydronicotinamide

AU - Versleijen, J.P.G.

AU - Sanders-Hovens, M.S.T.H.

AU - Vanhommerig, S.A.M.

AU - Vekemans, J.A.J.M.

AU - Meijer, E.M.

PY - 1993

Y1 - 1993

N2 - 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.

AB - 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.

U2 - 10.1016/S0040-4020(01)87253-7

DO - 10.1016/S0040-4020(01)87253-7

M3 - Article

SN - 0040-4020

VL - 49

SP - 7793

EP - 7802

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

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

Abstract

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