159279-77-3Relevant academic research and scientific papers
Synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids via base-induced cyclization of γ-chloro-α-imino ester
Boeykens,De Kimpe,Abbaspour Tehrani
, p. 6973 - 6985 (2007/10/02)
β-Chloro ketones were oxidatively transformed into α-keto carboxylic esters and condensed with primary amines in the presence of titanium(IV) chloride. Base-induced cyclization of the resulting γ-chloro-α-imino esters, incorporating suitable N-substituent
Straightforward Synthesis of 1-Amino-2,2-dialkylcyclopropanecarboxylic Acids via Selective Saponification of 2,2-Dialkylcyclopropane-1,1-dicarboxylic Esters and Curtius Rearrangement
De Kimpe, Norbert,Boeykens, Marc,Tehrani, Kourosch Abbaspour
, p. 8215 - 8219 (2007/10/02)
Selective monosaponification of dimethyl 2,2-dialkylcyclopropane-1,1-dicarboxylic esters afforded the corresponding 2,2-dialkyl-1-(methoxycarbonyl)cyclopropane-1-carboxylic acids, which were rearranged with diphenyl phosphoroazidate via a modified Curtius-type reaction to give methyl 2,2-dialkyl-1-cyclopropanecarboxylic esters.Selective deprotection of the carbamate or methyl cyclopropanecarboxylic ester was worked out, giving rise to a whole variety of ACC analogues.Straightforward ways to 1-amino-2,2-dialkylcyclopropanecarboxylic acids (2,2-dialkyl-ACC's) were developed.
