Stereoselective synthesis of both enantiomers of N-Boc-α-aryl-γ-aminobutyric acids

被引：18

作者：

Camps, P ^{[1
]}

Muñoz-Torrero, D ^{[1
]}

Sánchez, L ^{[1
]}

机构：

[1] Univ Barcelona, Lab Quim Farmaceut, Unitat Associada, CSIC,Fac Farm, E-08028 Barcelona, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 02期

关键词：

D O I：

10.1016/j.tetasy.2003.10.035

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Esterification of racemic alpha-aryl-beta-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (alphaR,3'R)- or (alphaS,3'S)-configured pantolactam cyano ester, respectively, in nearly quantitative yields with diastereomeric ratios of up to 93:7. Column chromatography of the diastereoenriched cyano esters, followed by hydrolysis of the resulting diastereopure cyano esters under essentially nonracemizing conditions gave enantiopure alpha-aryl-beta-cyanopropionic acids, which were readily converted in high yields into enantiopure (OER)- and (alphaS)-configured N-tert-butoxycarbonyl-alpha-aryl-gamma-aminobutyric acid (GABA) derivatives of potential biological interest. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：311 / 321

页数：11

共 24 条

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