Title
Straightforward synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids via selective saponification of 2,2-dialkylcycltopropane-1,1-dicarboxylic esters and curtius rearrangementStraightforward synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids via selective saponification of 2,2-dialkylcycltopropane-1,1-dicarboxylic esters and curtius rearrangement
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):26, p. 8215-8219
ISSN
0022-3263
ISI
A1994QA49200045
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Abstract
Selective monosaponification of dimethyl 2,2-dialkylcyclopropane-1,1l-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-[N-(alkoxycarbonyl)amino]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.
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