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 24 条

[1] Preparation of 2,3-epoxycycloalkanones from bicyclo [n.1.0]alkan-1-ols
Barnier, JP
Morisson, V
Blanco, L
SYNTHETIC COMMUNICATIONS, 2001, 31 (03) : 349 - 357
[2] Oxidative rearrangement of bicyclo[n.1.0]alkan-1-ols in the presence of oxygen.
Morisson, V
Barnier, JP
Blanco, L
TETRAHEDRON LETTERS, 1999, 40 (21) : 4045 - 4046
[3] A Convenient Transformation of 2-Alkylidenecycloalkanones into Alkyl-Substituted Bicyclo[n.1.0]alkan-1-ols: Application to the Synthesis of Capsaicin
Kananovich, Dzmitry G.
Zubrytski, Dzmitry M.
Kulinkovich, Oleg G.
SYNLETT, 2010, (07) : 1043 - 1046
[4] Preparation of optically active 2-(trifluoromethyl)alkan-1-ols by catalytic asymmetric hydrogenation
Iseki, K
Kuroki, Y
Nagai, T
Kobayashi, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (03) : 477 - 480
[5] A facile approach to bicyclo[n.2.0]alkan-1-ols:: An overview
Loughlin, WA
AUSTRALIAN JOURNAL OF CHEMISTRY, 2004, 57 (04) : 335 - 338
[6] PREPARATION OF OPTICALLY-ACTIVE 2-(TRIFLUOROMETHYL)ALKAN-1-OLS BY CATALYTIC ASYMMETRIC HYDROGENATION
ISEKI, K
KUROKI, Y
NAGAI, T
KOBAYASHI, Y
JOURNAL OF FLUORINE CHEMISTRY, 1994, 69 (01) : 5 - 6
[7] Preparation of optically active 2-(trifluoromethyl)alkan-1-ols by catalytic asymmetric hydrogenation (vol 44, pg 477, 1996)
Iseki, K
Kuroki, Y
Nagai, T
Kobayashi, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (06) : 1288 - 1288
[8] Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from Bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones
Zubrytski, D. M.
Kananovich, D. G.
Matiushenkov, E. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (06) : 813 - 823
[9] Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones
D. M. Zubrytski
D. G. Kananovich
E. A. Matiushenkov
Russian Journal of Organic Chemistry, 2017, 53 : 813 - 823
[10] The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide
Loughlin, WA
McCleary, MA
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (08) : 1347 - 1353

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