Tang Li-Wei, Zhao Bao-Jing, Dai Li, Zhang Man, Zhou Zhi-Ming
R&D Centre of Pharmaceuticals school of Chemical Engineering and the Environment, Beijing Institute of Technology, 5th Zhongguancun South Street, Haidian District, Beijing, China.
State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, 5th Zhongguancun South Street, Haidian District, Beijing, China.
Chem Asian J. 2016 Sep 6;11(17):2470-7. doi: 10.1002/asia.201600941. Epub 2016 Aug 25.
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, Cu(I) /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.
已开发出一种直接且简便的方法，用于合成在吡咯烷环的C-3位带有含CF3基团的季碳立体中心的光学活性吡咯烷。该合成体系，即Cu(I)/Si-FOXAP催化的甲亚胺叶立德与β-CF3-β,β-二取代硝基烯烃的外型选择性1,3-偶极环加成反应，能提供具有高非对映选择性（高达>98:2的非对映体比例）和优异对映选择性（高达>99.9% ee）的吡咯烷，并且在温和条件下对多种底物都表现良好。
