Facile stereoselective synthesis of gamma-substituted gamma-amino acids from the corresponding alpha-amino acids

被引：69

作者：

Smrcina, M

Majer, P

Majerova, E

Guerassina, TA

Eissenstat, MA

机构：

[1] Structural Biochemistry Program, National Cancer Institute, Frederick Cancer R. and D. Center, Frederick

来源：

TETRAHEDRON | 1997年 / 53卷 / 38期

关键词：

D O I：

10.1016/S0040-4020(97)00840-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile stereoselective method for the synthesis of gamma-substituted, gamma-amino acids from alpha-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of alpha-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields, the corresponding gamma-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%. (C) 1997 Elsevier Science Ltd.

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页码：12867 / 12874

页数：8

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