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Title
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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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Author
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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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Language
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English
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Source (journal)
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The journal of organic chemistry. - Washington, D.C., 1936, currens
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Publication
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Washington, D.C.
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1994
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ISSN
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0022-3263
[print]
1520-6904
[online]
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DOI
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10.1021/JO00105A045
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Volume/pages
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59
:26
(1994)
, p. 8215-8219
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ISI
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A1994QA49200045
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Full text (Publisher's DOI)
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