ENANTIOSELECTIVE CONJUGATE REDUCTION OF ALPHA,BETA-UNSATURATED CARBOXAMIDES WITH SEMICORRIN COBALT CATALYSTS

被引：50

作者：

VONMATT, P ^{[1
]}

PFALTZ, A ^{[1
]}

机构：

[1] UNIV BASEL,INST ORGAN CHEM,S JOHANNS RING 19,CH-4056 BASEL,SWITZERLAND

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(00)86123-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral semicorrin cobalt complexes, prepared in situ from cobalt(II) chloride and the free ligands, are efficient, highly enantioselective catalysts for the conjugate reduction of alpha,beta-unsaturated carboxamides with sodium borohydride. Enantiomeric excesses of up to 99 %, essentially quantitative yields, and high substrate/catalyst ratios (1 000 - 10 000:1) are attractive attributes of this catalytic process.

引用

页码：691 / 700

页数：10

共 29 条

[1] LIQUID-CHROMATOGRAPHIC ANALYSIS OF ENANTIOMERIC PURITY OF SEVERAL TERPENOID ACIDS AS THEIR 1-(1-NAPHTHYL)ETHYLAMIDE DERIVATIVES
BERGOT, BJ
ANDERSON, RJ
SCHOOLEY, DA
HENRICK, CA
[J]. JOURNAL OF CHROMATOGRAPHY, 1978, 155 (01): : 97 - 105
[2] SELECTIVE REDUCTIONS .30. EFFECT OF CATION AND SOLVENT ON THE REACTIVITY OF SALINE BOROHYDRIDES FOR REDUCTION OF CARBOXYLIC ESTERS - IMPROVED PROCEDURES FOR THE CONVERSION OF ESTERS TO ALCOHOLS BY METAL BOROHYDRIDES
BROWN, HC
NARASIMHAN, S
CHOI, YM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) : 4702 - 4708
[3] DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX
COREY, EJ
IMAI, N
ZHANG, HY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 728 - 729
[4] COUTROT P, 1978, SYNTHESIS-STUTTGART, P133
[5] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS
EVANS, DA
WOERPEL, KA
HINMAN, MM
FAUL, MM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 726 - 728
[6] COB(I)ALAMIN AS CATALYST .5. ENANTIOSELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL DERIVATIVES
FISCHLI, A
SUSS, D
[J]. HELVETICA CHIMICA ACTA, 1979, 62 (07) : 2361 - 2373
[7] SEMICORRIN METAL-COMPLEXES AS ENANTIOSELECTIVE CATALYSTS .1. SYNTHESIS OF CHIRAL SEMICORRIN LIGANDS AND GENERAL CONCEPTS
FRITSCHI, H
LEUTENEGGER, U
SIEGMANN, K
PFALTZ, A
KELLER, W
KRATKY, C
[J]. HELVETICA CHIMICA ACTA, 1988, 71 (06) : 1541 - 1552
[8] CHIRAL COPPER SEMICORRIN COMPLEXES AS ENANTIOSELECTIVE CATALYSTS FOR THE CYCLOPROPANATION OF OLEFINS BY DIAZO-COMPOUNDS
FRITSCHI, H
LEUTENEGGER, U
PFALTZ, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (11): : 1005 - 1006
[9] SEMICORRIN METAL-COMPLEXES AS ENANTIOSELECTIVE CATALYSTS .2. ENANTIOSELECTIVE CYCLOPROPANE FORMATION FROM OLEFINS WITH DIAZO-COMPOUNDS CATALYZED BY CHIRAL (SEMICORRINATO)COPPER COMPLEXES
FRITSCHI, H
LEUTENEGGER, U
PFALTZ, A
[J]. HELVETICA CHIMICA ACTA, 1988, 71 (06) : 1553 - 1565
[10] Fritschi H., 1986, ANGEW CHEM, V98, P1028

← 1 2 3 →