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Ring Opening of Bicyclo[3.1.0]hexan‐2‐ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates
Author(s) -
Feierfeil Johannes,
Grossmann Adriana,
Magauer Thomas
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201506232
Subject(s) - conrotatory and disrotatory , aromatization , benzoates , bicyclic molecule , ring (chemistry) , chemistry , organic chemistry , combinatorial chemistry , catalysis
Described is the development of a highly efficient 2π disrotatory ring‐opening aromatization sequence using bicyclo[3.1.0]hexan‐2‐ones. This unprecedented transformation efficiently proceeds under thermal conditions and allows facile construction of uniquely substituted and polyfunctionalized benzoates. In the presence of either amines or alcohols formation of substituted anilines or ethers, respectively, is achieved. Additionally, the utility of this method was demonstrated in a short synthesis of sekikaic acid methyl ester.