Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates

Article abstract of DOI:10.1002/anie.201506232

Described is the development of a highly efficient 2πdisrotatory 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. Cracked open: A highly efficient thermal 2πdisrotatory ring-opening aromatization sequence of bicyclo[3.1.0]hexan-2-ones is described. The transformation proceeds in sulfolane to give uniquely substituted benzoates. In the presence of either amines or alcohols, formation of substituted anilines or ethers, respectively, is achieved.