Asymmetric Construction of Pyrrolidines Bearing a Trifluoromethylated Quaternary Stereogenic Center via CuI‐Catalyzed 1,3‐Dipolar Cycloaddition of Azomethine Ylides with β‐CF3‐β,β‐Disubstituted Nitroalkenes |
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| Authors: | Dr Li‐Wei Tang Bao‐Jing Zhao Li Dai Man Zhang Prof?Dr Zhi‐Ming Zhou |
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| Institution: | 1. R&D Centre of Pharmaceuticals school of Chemical Engineering and the Environment, Beijing Institute of Technology, Beijing, China;2. State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing, China |
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| Abstract: | A direct and convenient method has been developed for the synthesis of optically active pyrrolidines bearing a quaternary stereogenic center containing a CF3 group at the C‐3 position of the pyrrolidine ring. The synthesis system, CuI/Si‐FOXAP‐catalyzed exo‐selective 1,3‐dipolar cycloaddition of azomethine ylides with β‐CF3‐β,β‐disubstituted nitroalkenes, provides pyrrolidines with high diastereoselectivities (up to >98:2 d.r.) and excellent enantioselectivities (up to >99.9 ee) and performs well for a broad scope of substrates under mild conditions. |
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| Keywords: | copper cycloaddition ferrocenyloxazolinylphosphines pyrrolidine trifluoromethylation |
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