CHEMOENZYMATIC SYNTHESIS OF ALL ISOMERIC 3-PHENYLSERINES AND 3-PHENYL-ISOSERINES

被引：68

作者：

HONIG, H

SEUFERWASSERTHAL, P

WEBER, H

机构：

[1] Institute of Organic Chemistry, Graz University of Technology, A-8010 Graz

来源：

TETRAHEDRON | 1990年 / 46卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(01)90519-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of all isomers of 3-phenylserines and 3-phenylisoserines in enantiomerically pure form is presented. Diastereomerically pure educts (threo/erythro-2-azido-3-butanoyoxy-3-phenyl-propionic esters, threo/erythro-3-azido-2-butanoyloxy-3-phenylpropionic esters, threo-2-butanoylamino-3-butanoyloxy-3-phenylpropionic ester, erythro-3-butanoylamino-2-butanoyloxy-3-phenyl-propionamide) were prepared from cinnamic acid derivatives or via aldol condensations of benzaldehyde and suitable enolates in few steps. These racemates were resolved with lipases from Candida cylindracea (CC) and Pseudomonas fluorescens (P) and the obtained products were hydrogenated to 3-phenylserines and -isoserines. The influence of the acyl group in the enzymatic resolution of erythro-3-azido-2-acyloxy-3-phenylpropionic esters was investigated. © 1990.

引用

页码：3841 / 3850

页数：10

共 51 条

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