Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions

被引：33

作者：

Paizs, C

Tosa, M

Bódai, V

Szakács, G

Kmecz, I

Simándi, B

Majdik, C

Novák, L

Irimie, FD

Poppe, L

机构：

[1] Univ Babes Bolyai, Dept Biochem & Biochem Engn, RO-3400 Cluj Napoca, Romania

[2] Budapest Univ Technol & Econ, Hungarian Acad Sci, Inst Organ Chem, H-1111 Budapest, Hungary

[3] Budapest Univ Technol & Econ, Hungarian Acad Sci, Res Grp Alkaloid Chem, H-1111 Budapest, Hungary

[4] Budapest Univ Technol & Econ, Dept Agr Chem Technol, H-1111 Budapest, Hungary

[5] Budapest Univ Technol & Econ, Dept Chem Engn, H-1521 Budapest, Hungary

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 13期

基金：

匈牙利科学研究基金会;

关键词：

D O I：

10.1016/S0957-4166(03)00358-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Kinetic resolution of racemic 1-(benzofuran-2-yl)ethanols rac-1a-d was performed by lipase-catalyzed enantiomer selective acylation (Emuch greater than100) yielding (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d and (1S)-1-(benzofuran-2-yl)ethanois (S)-1a-d in highly enantiopure form. The degree of enantiomer selectivity for enzymatic alcoholysis/hydrolysis processes starting from racemic 1-acetoxy-1-(benzofuran-2-yl)ethane rac-2 was also tested under various conditions including supercritical CO2 medium. Racemization-free lipase-catalyzed ethanolysis of the (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a-d yielded almost quantitatively the enantiopure (1R)-1-(benzofuran-2-yl)ethanols (R)-1a-d. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1943 / 1949

页数：7

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