title: Asymmetric Construction of Pyrrolidines Bearing a Trifluoromethylated Quaternary Stereogenic Center via Cu(I) -Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-CF3 -β,β-Disubstituted Nitroalkenes.
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, 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.
authors.affiliation: R&D Centre of Pharmaceuticals school of Chemical Engineering and the Environment, Beijing Institute of Technology, 5th Zhongguancun South Street, Haidian District, Beijing, China.
authors.forename: Li-Wei
authors.initials: LW
authors.lastname: Tang
authors.affiliation: R&D Centre of Pharmaceuticals school of Chemical Engineering and the Environment, Beijing Institute of Technology, 5th Zhongguancun South Street, Haidian District, Beijing, China.
authors.forename: Bao-Jing
authors.initials: BJ
authors.lastname: Zhao
authors.affiliation: R&D Centre of Pharmaceuticals school of Chemical Engineering and the Environment, Beijing Institute of Technology, 5th Zhongguancun South Street, Haidian District, Beijing, China.
authors.forename: Li
authors.initials: L
authors.lastname: Dai
authors.affiliation: R&D Centre of Pharmaceuticals school of Chemical Engineering and the Environment, Beijing Institute of Technology, 5th Zhongguancun South Street, Haidian District, Beijing, China.
authors.forename: Man
authors.initials: M
authors.lastname: Zhang
authors.affiliation: R&D Centre of Pharmaceuticals school of Chemical Engineering and the Environment, Beijing Institute of Technology, 5th Zhongguancun South Street, Haidian District, Beijing, China. zzm@bit.edu.cn.|State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, 5th Zhongguancun South Street, Haidian District, Beijing, China. zzm@bit.edu.cn.
authors.forename: Zhi-Ming
authors.initials: ZM
authors.lastname: Zhou
keywords: copper; cycloaddition; ferrocenyloxazolinylphosphines; pyrrolidine; trifluoromethylation