Lipase-catalyzed solvent-free kinetic resolution of substituted racemic ε-caprolactones

被引：23

作者：

Kondaveti, L ^{[1
]}

Al-Azemi, TF ^{[1
]}

Bisht, KS ^{[1
]}

机构：

[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(02)00064-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The kinetic resolution of racemic seven-membered lactones is reported, for the first time in bulk (solvent-free) conditions, by lipase-catalysed butanolysis. The lactones studied were substituted at either the 4- or the 6-position. With these lactones, Novozym-435 lipase (from Candida antarctica) induced (S)-selective butanololysis, and (R)-lactones were recovered unreacted with >97% enantiomeric excess (e.e.). The reactions were studied at different reaction temperatures, viz. 0, 23, 40 and 60degreesC. A comparative study of the effect of temperature on the kinetic resolution is presented. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：129 / 135

页数：7

相关论文

共 47 条

[1] Enzyme-catalyzed ring-opening copolymerization of 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one (MBC) with trimethylene carbonate (TMC): Synthesis and characterization [J].

Al-Azemi, TF ;

Harmon, JP ;

Bisht, KS .

BIOMACROMOLECULES, 2000, 1 (03) :493-500

[2] Novel functional polycarbonate by lipase-catalyzed ring-opening polymerization of 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one [J].

Al-Azemi, TF ;

Bisht, KS .

MACROMOLECULES, 1999, 32 (20) :6536-6540

[3] One biocatalyst - Many applications: The use of Candida antarctica B-lipase in organic synthesis [J].

Anderson, EM ;

Karin, M ;

Kirk, O .

BIOCATALYSIS AND BIOTRANSFORMATION, 1998, 16 (03) :181-204

[4] HIGH ENANTIOSELECTIVE ESTERIFICATION OF 2-ARYLPROPIONIC ACIDS CATALYZED BY IMMOBILIZED LIPASE FROM CANDIDA-ANTARCTICA - A MECHANISTIC APPROACH [J].

ARROYO, M ;

SINISTERRA, JV .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4410-4417

[5] Lipase-catalyzed ring-opening polymerization of trimethylene carbonate [J].

Bisht, KS ;

Svirkin, YY ;

Henderson, LA ;

Gross, RA ;

Kaplan, DL ;

Swift, G .

MACROMOLECULES, 1997, 30 (25) :7735-7742

[6] Ethyl glucoside as a multifunctional initiator for enzyme-catalyzed regioselective lactone ring-opening polymerization [J].

Bisht, KS ;

Deng, F ;

Gross, RA ;

Kaplan, DL ;

Swift, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) :1363-1367

[7] Enzyme-catalyzed ring-opening polymerization of omega-pentadecalactone [J].

Bisht, KS ;

Henderson, LA ;

Gross, RA ;

Kaplan, DL ;

Swift, G .

MACROMOLECULES, 1997, 30 (09) :2705-2711

[8] ENZYMATIC RESOLUTION OF RACEMIC LACTONES [J].

BLANCO, L ;

GUIBEJAMPEL, E ;

ROUSSEAU, G .

TETRAHEDRON LETTERS, 1988, 29 (16) :1915-1918

[9] OPTICALLY-ACTIVE LACTONES FROM A BAEYER-VILLIGER-TYPE METAL-CATALYZED OXIDATION WITH MOLECULAR-OXYGEN [J].

BOLM, C ;

SCHLINGLOFF, G ;

WEICKHARDT, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (18) :1848-1849

[10] INFLUENCES OF REACTION CONDITIONS ON THE ENANTIOSELECTIVE TRANSESTERIFICATION USING PSEUDOMONAS-CEPACIA LIPASE [J].

BORNSCHEUER, U ;

SCHAPOHLER, S ;

SCHEPER, T ;

SCHUGERL, K .

TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :1011-1014

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