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Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids via base-induced cyclization of -chloro--imino esters
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| Abstract |
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| 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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English
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The journal of organic chemistry. - Washington, D.C. | |
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Washington, D.C. : 1994
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0022-3263
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59:23(1994), p. 6973-6985
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| ISI |
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A1994PT81200022
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