Synthesis of gamma-oxo alpha-amino acids from L-aspartic acid

被引：40

作者：

Golubev, AS

Sewald, N

Burger, K

机构：

[1] UNIV LEIPZIG,INST ORGAN CHEM,D-04103 LEIPZIG,GERMANY

[2] RUSSIAN ACAD SCI,AN NESMEYANOV ORGANOELEMENT CPDS INST,MOSCOW 117813,RUSSIA

来源：

TETRAHEDRON | 1996年 / 52卷 / 47期

关键词：

L-aspartic acid; gamma-oxo alpha-amino acids; 5-hydroxy-4-oxo-norvaline; 4-oxo-L-pipecolic acid; Stille reaction; intramolecular Michael addition; hexafluoroacetone;

D O I：

10.1016/0040-4020(96)00942-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of different gamma-oxo alpha-amino acids from hexafluoroacetone protected L-aspartic acid chloride 1 via Stille cross coupling reaction is described. Stille reaction of 1 with vinyltributyltin followed by Lewis acid catalyzed intramolecular Michael addition provides access to 4-substituted pipecolic acid derivatives. An efficient synthesis of 5-hydroxy-4-oxo-L-norvaline 7 and a new approach to the 4-oxo-L-ornithine skeleton starting from 1 have been elaborated. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：14757 / 14776

页数：20

共 84 条

[1] ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES [J].