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

被引：24

作者：

VERSLEIJEN, JP

SANDERSHOVENS, MS

VANHOMMERIG, SA

VEKEMANS, JA

MEIJER, EM

机构：

[1] Laboratory of Organic Chemistry, Eindhoven University of Technology, 5600 MB Eindhoven

来源：

TETRAHEDRON | 1993年 / 49卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)87253-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha-keto esters and alpha-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.

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收藏

页码：7793 / 7802

页数：10

相关论文

共 31 条

[1] ON THE STRUCTURE OF N-METHYLENECARBOXAMIDES - X-RAY DATA, SPECTROSCOPY, AND QUANTUM-MECHANICAL CALCULATIONS [J].

ALLMANN, R ;

KUPFER, R ;

NAGEL, M ;

WURTHWEIN, EU .

CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (04) :1597-1605

[2]

ANDERSON RC, 1984, J ORG CHEM, V49, P1304, DOI 10.1021/jo00181a042

[3]

BEIJER NA, 1990, RECL TRAV CHIM PAY B, V109, P434

[4]

BIGG DCH, 1992, SYNTHESIS-STUTTGART, P277

[5] SYNTHESIS OF N-ACYL, N-SULFONYL, AND "N-PHOSPHINYLPHOSPHA-LAMBDA-5-AZENES BY A REDOX-CONDENSATION REACTION USING AMIDES, TRIPHENYLPHOSPHINE, AND DIETHYL AZODICARBOXYLATE [J].

BITTNER, S ;

ASSAF, Y ;

KRIEF, P ;

POMERANTZ, M ;

ZIEMNICKA, BT ;

SMITH, CG .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1712-1718

[6] TRIHALOGENOMETHYL COMPOUNDS OF POTENTIAL THERAPEUTIC INTEREST .4. [J].

BOWMAN, RE ;

CLOSIER, MD ;

ISLIP, PF .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (OCT) :3841-&

[7] 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

[8] 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

[9] ASYMMETRIC REDUCTIONS WITH FREELY AND NON-FREELY ROTATING AMIDE GROUP NADH MODELS [J].

COMBRET, Y ;

TORCHE, JJ ;

BINAY, P ;

DUPAS, G ;

BOURGUIGNON, J ;

QUEGUINER, G .

CHEMISTRY LETTERS, 1991, (01) :125-128

[10] SYNTHESIS AND REACTIVITY OF PROTECTED BETA-BROMO ALPHA-IMINOACIDS - A CONVENIENT ROUTE TO STRUCTURALLY DIVERSIFIED AMINO-ACIDS [J].

DANIONBOUGOT, R ;

DANION, D ;

FRANCIS, G .

TETRAHEDRON LETTERS, 1990, 31 (26) :3739-3742

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