ENANTIOSELECTIVE REDUCTION OF C=O AND C=N COMPOUNDS WITH NADH MODEL N,N,1,2,4-PENTAMETHYL-1,4-DIHYDRONICOTINAMIDE

Authors
VERSLEIJEN JP SANDERSHOVENS MS VANHOMMERIG SA VEKEMANS JA MEIJER EM
Citation
Jp. Versleijen et al., ENANTIOSELECTIVE REDUCTION OF C=O AND C=N COMPOUNDS WITH NADH MODEL N,N,1,2,4-PENTAMETHYL-1,4-DIHYDRONICOTINAMIDE, Tetrahedron, 49(35), 1993, pp. 7793-7802
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
35
Year of publication
1993
Pages
7793 - 7802
Database
ISI
SICI code
0040-4020(1993)49:35<7793:EROCAC>2.0.ZU;2-U
Abstract
The scope and mechanism of enantioselective hydride transfer from NADH model 4 to prochiral C=O and C=N compounds were investigated. Efficie nt chirality transfer from 4 to alpha-keto esters and alpha-methoxycar bonylimino esters was achieved. The resemblance in reactivity and ster eochemistry of the prochiral C=O and C=N-CO2Me functionalities in the hydride transfer reaction is attributed to the intervention of a simil ar Mg(ClO4)2-mediated ternary complex.