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Straightforward synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids via selective saponification of 2,2-dialkylcycltopropane-1,1-dicarboxylic esters and curtius rearrangement
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| Abstract |
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| 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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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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59:26(1994), p. 8215-8219
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A1994QA49200045
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