CHARACTERIZATION OF ALPHA-HALO-IMINE INTERMEDIATES DERIVED FROM HALOGENATION OF DEHYDROAMINO ACID-DERIVATIVES

被引：27

作者：

COMBS, AP ^{[1
]}

ARMSTRONG, RW ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(00)79004-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot Erlenmeyer-Plochl reaction affords high yields of optically active aliphatic dehydroamino acid derivatives. Subsequent halogenation with NBS or NIS yields the alpha-halo-imine derivatives which undergo kinetically controlled tautomerization with Et3N, resulting in increased E selectivity. Isomerization of these derivatives in the presence of strong base (DABCO) results in exclusive formation of the more stable Z vinyl bromides. High yields of the beta-halo-dehydroamino acids are obtained in all cases.

引用

页码：6419 / 6422

页数：4

共 14 条

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