Umpolung of Imines Enables Catalytic Asymmetric Regio‐reversed [3+2] Cycloadditions of Iminoesters with Nitroolefins

作者：Bin Feng, Liang‐Qiu Lu, Jia‐Rong Chen, Guoqiang Feng, Bin‐Qing He, Bin Lu, Wen‐Jing Xiao · 发表于：Angewandte Chemie International Edition · 年份：2018 · DOI：10.1002/anie.201802492 · 被引用次数：71 · 研究领域：Synthesis and Catalytic Reactions、Asymmetric Synthesis and Catalysis、Catalytic C–H Functionalization Methods

A copper-catalyzed regio-reversed asymmetric [3+2] cycloaddition of iminoesters with nitroolefins is disclosed for the first time. This method enables the facile synthesis of polysubstituted chiral pyrrolidines bearing at least one chiral quaternary center in high yields with excellent regio-, diastereo-, and enantioselectivity. The application of chiral P,S ligands and the unique effect of α-aryl groups on the iminoesters are key to the success of this method. The practicality and versatility of the reaction are also demonstrated.