Journal
TETRAHEDRON
Volume 61, Issue 5, Pages 1207-1219Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.11.037
Keywords
cyclohex-3-ene carboxylic acid; Curtius rearrangement; diphenylphosphoryl azide; alkyl N-(1-cyclohex-3-enyl)carbamates; epoxides; ringopening
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The Curtius rearrangement of cyclohex-3-ene carboxylic acid using diphenylphosphoryl azide in the presence of triethylamime and ethanol, t-butanol or benzyl alcohol has been described. As a result the synthesis of ethyl, t-butyl or benzyl N-(1-cyclohex-3-enyl)carbamates has been achieved in one pot, in good chemical yield. A series of transformations of benzyl N-(1-cyclohex-3-enyl)carbamate, such as iodination and epoxidation, as well as opening of the corresponding ring epoxide, have been carried out leading to some useful oxygenated cyclohexylamimo building blocks. (C) 2004 Elsevier Ltd. All rights reserved.
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