Improved process for the enantioselective hydrolysis of prochiral diethyl malonates catalyzed by pig liver esterase

被引：17

作者：

de María, PD

Kossmann, B

Potgrave, N

Buchholz, S

Trauthwein, H

May, O

Gröger, H

机构：

[1] Degussa AG, Serv Ctr Biocatalysis, D-63457 Hanau, Germany

[2] Degussa AG, Project House Proferm, D-45764 Marl, Germany

来源：

SYNLETT | 2005年 / 11期

关键词：

asymmetric synthesis; enzymes; hydrolyses; malonates; solvent effects;

D O I：

10.1055/s-2005-871548

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved process for the enantioselective hydrolysis of prochiral 2-aryl-2-alkyl-disubstituted diethyl malonates catalyzed by pig liver esterase (PLE) was developed. With diethyl 2phenyl-2-methylmalonate as a model substrate, the highest enantioselectivities (96% ee; R-isomer) were achieved when carrying out the process in the presence of a suitable mixture of cosolvents (buffer-i-PrOH-t-BuOH, 8: 1: 1). The process also works efficiently at higher substrate concentrations. The reaction was carried out on a multi-gram preparative scale, leading to a conversion of > 95%, an enantioselectivity of 96% ee, and a yield of 83% at a substrate concentration of 200 mM.

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收藏

页码：1746 / 1748

页数：3

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