AN APPROACH TO FEATURES RESPONSIBLE FOR THE OBTENTION OF HIGH EE WITH A HIGHLY ENANTIOSELECTIVE NADH MODEL

被引：27

作者：

COMBRET, Y

DUFLOS, J

DUPAS, G

BOURGUIGNON, J

QUEGUINER, G

机构：

[1] URA 1429 CNRS/Institut National des Sciences Appliquées, 76131 Mont Saint Aignan

来源：

TETRAHEDRON | 1993年 / 49卷 / 24期

关键词：

NADH MODELS; ASYMMETRIC REDUCTION; FREE ROTATING ABILITY; ENTROPY;

D O I：

10.1016/S0040-4020(01)82373-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A study of the reactivity of several NADH models with free, restricted or suppressed rotating ability of the amide carbonyl group suggests that the main factor responsible for the high e.e. obtained (94 %) with a cyclized reagent is an entropy feature.

引用

收藏

页码：5237 / 5246

页数：10

相关论文

共 16 条

[1]

BABA N, 1983, ASYMMETRIC SYNTHESIS, V2, P90

[2] INVERSION IN THE ENANTIOSELECTIVITY OF REDUCTIONS PERFORMED WITH NADH MODELS BEARING THE SAME CHIRAL AUXILIARY [J].

BINAY, P ;

DUPAS, G ;

BOURGUIGNON, J ;

QUEGUINER, G .

TETRAHEDRON LETTERS, 1988, 29 (08) :931-932

[3] NADH MIMICS FOR THE STEREOSELECTIVE REDUCTION OF BENZOYLFORMATES TO THE CORRESPONDING MANDELATES [J].

BURGESS, VA ;

DAVIES, SG ;

SKERLJ, RT .

TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :299-328

[4] STEREOSELECTIVITY OF HYDROGEN TRANSFER WITH CHIRAL NADH MODELS AS A FUNCTION OF CONFIGURATION AND CONFORMATION [J].

COMBRET, Y ;

TORCHE, JJ ;

PLE, N ;

DUFLOS, J ;

DUPAS, G ;

BOURGUIGNON, J ;

QUEGUINER, G .

TETRAHEDRON, 1991, 47 (45) :9369-9382

[5] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[6] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[7] HIGHLY REACTIVE AND STEREOSELECTIVE (R) AND (S)-3-(N,N-DIMETHYLCARBAMOYL)-1,2,4-TRIMETHYL-1,4-DIHYDROPYRIDINES FOR NADH NAD+ MIMICRY [J].

DEKOK, PMT ;

BASTIAANSEN, LAM ;

VANLIER, PM ;

VEKEMANS, JAJM ;

BUCK, HM .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1313-1320

[8]

DUGAS H, 1988, BIOORGANIC CHEM CHEM, P187

[9]

FERSHT A, 1977, ENZYME STRUCTURE MEC, P44

[10] METAL-ION FUNCTION IN ALCOHOL DEHYDROGENASES .1. METAL-DEPENDENT REDUCTION OF PYRIDINE CARBALDEHYDES [J].

HUGHES, M ;

PRINCE, RH .

JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1978, 40 (04) :703-712