Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates
Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates
复制标题
DOI：
10.1002/anie.201506232
复制
发表时间：
2015-09-28
影响因子：
16.6
通讯作者：
Magauer, Thomas
中科院分区：
文献类型：
--
作者：
Feierfeil, Johannes;Grossmann, Adriana;Magauer, Thomas
描述了使用双环[3.1.0]己-2-酮的高效2 π对旋开环芳构化序列的开发。这种前所未有的转化在热条件下有效地进行，并允许简单地构建独特取代和多官能化的苯甲酸酯。在胺或醇的存在下，分别形成取代的苯胺或醚。此外，该方法的实用性被证明在短合成关酸甲酯。
Described is the development of a highly efficient 2 pi 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.