Umpolung of Imines Enables Catalytic Asymmetric Regio‐reversed [3+2] Cycloadditions of Iminoesters with Nitroolefins |
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Authors: | Bin Feng Liang‐Qiu Lu Jia‐Rong Chen Guoqiang Feng Bin‐Qing He Bin Lu Wen‐Jing Xiao |
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Institution: | 1. http://chem‐xiao.ccnu.edu.cn/;2. CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei, China |
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Abstract: | 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. |
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Keywords: | chiral ligands cycloaddition imines nitroolefins umpolung |
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