Formal Carbene Insertion into C–C Bond: Rh(I)-Catalyzed Reaction of Benzocyclobutenols with Diazoesters

A Rh­(I)-catalyzed formal carbene insertion into C–C bond of benzocyclobutenols has been realized by employing diazoesters as carbene precursors. The product indanol derivatives were obtained in good yields and in diastereoselective manner under mild reaction conditions. All-carbon quaternary center is constructed at the carbenic carbon. This catalytic reaction involves selective cleavage of C–C bond, Rh­(I) carbene insertion, and intramolecular aldol reaction.

本研究实现了以重氮酯为卡宾前体的铑(I)催化苯并环丁醇碳-碳键形式卡宾插入反应。目标产物茚满醇衍生物可在温和反应条件下以良好收率及优异非对映选择性得到，反应在卡宾碳位点构建了全碳季碳中心。该催化反应涉及选择性碳-碳键断裂、铑(I)卡宾插入以及分子内羟醛反应三个关键步骤。