SYNTHESIS OF 1-AMINO-2,2-DIALKYLCYCLOPROPANECARBOXYLIC ACIDS VIA BASE-INDUCED CYCLIZATION OF GAMMA-CHLORO-ALPHA-IMINO ESTERS

被引：32

作者：

BOEYKENS, M ^{[1
]}

DEKIMPE, N ^{[1
]}

TEHRANI, KA ^{[1
]}

机构：

[1] STATE UNIV GHENT,FAC AGR & APPL BIOL SCI,DEPT ORGAN CHEM,B-9000 GHENT,BELGIUM

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 23期

关键词：

D O I：

10.1021/jo00102a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Chloro ketones were oxidatively transformed into alpha-keto carboxylic esters and condensed with primary amines in the presence of titanium(IV) chloride. Base-induced cyclization of the resulting gamma-chloro-alpha-imino esters, incorporating suitable N-substituents, led directly to 1-amino-2,2-dialkyl- cyclopropanecarboxylic ester derivatives via a 1,5-dehydrochlorination process. Syntheses of different N- and/or carboxyl-protected geminally (gem) dialkylated cyclopropane amino acids were developed, while access to the free alpha-amino acids is also given. The methodology used was further extended by reduction of the gamma-chloro-alpha-imino esters to functionalized gamma-chloro-alpha-amino esters,prior to ring closure, affording N-alkyl-gem-dialkyl-1-aminocyclopropanecarboxylic acid derivatives.

引用

页码：6973 / 6985

页数：13

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