Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives:: Preparation of optically active α-substituted α-methylcycloalkanones.

被引：16

作者：

Morisson, V ^{[1
]}

Barnier, JP ^{[1
]}

Blanco, L ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Mol Orsay, Lab Carbocycles, Associe CNRS, F-91405 Orsay, France

来源：

TETRAHEDRON | 1998年 / 54卷 / 27期

关键词：

D O I：

10.1016/S0040-4020(98)00411-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active alpha-methyl alpha-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme(R)-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7749 / 7764

页数：16

共 55 条

[1] Stereocontrolled elaboration of quaternary carbon centers involving the asymmetric Michael-type alkylation of chiral imines: An efficient enantioselective access to (+)-vincamine
Alves, JCF
Simas, ABC
Costa, PRR
dAngelo, J
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (12) : 1963 - 1966
[2] ENZYMATIC RESOLUTION OF CYCLOPROPANOLS - AN EASY ACCESS TO OPTICALLY-ACTIVE CYCLOHEXANONES POSSESSING AN ALPHA-QUATERNARY CHIRAL CARBON
BARNIER, JP
BLANCO, L
ROUSSEAU, G
GUIBEJAMPEL, E
FRESSE, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) : 1570 - 1574
[3] ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES
CAIN, CM
COUSINS, RPC
COUMBARIDES, G
SIMPKINS, NS
[J]. TETRAHEDRON, 1990, 46 (02) : 523 - 544
[4] SYNTHESIS OF MEDIUM RING ETHERS .2. SYNTHESIS OF THE FULLY SATURATED CARBON SKELETON OF LAURENCIA NON-TERPENOID ETHER METABOLITES CONTAINING 7-MEMBERED, 8-MEMBERED AND 9-MEMBERED RINGS
CARLING, RW
CLARK, JS
HOLMES, AB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (01): : 83 - 94
[5] METHYL-METHACRYLATE AS ACCEPTOR IN THE ASYMMETRIC MICHAEL REACTION USING CHIRAL BETA-ENAMINOESTERS - SIMULTANEOUS, COMPLETE STEREOCONTROL OF A QUATERNARY CARBON CENTER AND A TERTIARY ONE IN THE BETA-POSITION
CAVE, C
DALEY, V
DANGELO, J
GUINGANT, A
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (01) : 79 - 82
[6] A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .1. FROM SIMPLE ALDEHYDES AND KETONES
CAZEAU, P
DUBOUDIN, F
MOULINES, F
BABOT, O
DUNOGUES, J
[J]. TETRAHEDRON, 1987, 43 (09) : 2075 - 2088
[7] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTION OF ENANTIOMERS .2. ENZYME-CATALYZED ESTERIFICATIONS IN WATER ORGANIC-SOLVENT BIPHASIC SYSTEMS
CHEN, CS
WU, SH
GIRDAUKAS, G
SIH, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) : 2812 - 2817
[8] COREY EJ, 1976, TETRAHEDRON LETT, P3
[9] TOTAL SYNTHESIS OF PICROTOXININ
COREY, EJ
PEARCE, HL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (19) : 5841 - 5843
[10] THE ASYMMETRIC MICHAEL ADDITION-REACTIONS USING CHIRAL IMINES
DANGELO, J
DESMAELE, D
DUMAS, F
GUINGANT, A
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (04) : 459 - 505

← 1 2 3 4 5 6 →