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

• Published in: Chemistry, an Asian journal an Asian journal, 2016-09, Vol.11 (17), p.2470-2477
• Main Authors: Tang, Li-Wei, Zhao, Bao-Jing, Dai, Li, Zhang, Man, Zhou, Zhi-Ming
• Format: Article
• Language: English
• Subjects: copper; cycloaddition; ferrocenyloxazolinylphosphines; pyrrolidine; trifluoromethylation
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.201600941

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. Direct and convenient: Synthesis of optically active pyrrolidines bearing a quaternary stereogenic center containing a CF3 group at the C‐3 position of the pyrrolidine ring has been reported. The products were obtained with high diastereoselectivities (up to >98:2 d.r.) and excellent enantioselectivities (up to >99.9 ee).