Title
Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids via base-induced cyclization of <tex>$\gamma$</tex>-chloro-<tex>$\alpha$</tex>-imino esters
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Washington, D.C. ,
Subject
Chemistry
Source (journal)
The journal of organic chemistry. - Washington, D.C.
Volume/pages
59(1994) :23 , p. 6973-6985
ISSN
0022-3263
ISI
A1994PT81200022
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Abstract
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.
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