title: Diastereo- and Enantioselective Copper(I)-Catalyzed Intermolecular [3+2] Cycloaddition of Azomethine Ylides with β-Trifluoromethyl β,β-Disubstituted Enones.
abstract: Reported herein is an asymmetric [3+2] cycloaddition reaction of azomethine ylides with β-trifluoromethyl β,β-disubstituted enones, a reaction which is enabled by a Ming-Phos-derived copper(I) catalyst (Ming-Phos=chiral sulfinamide monophosphines, Figure ). This method provides scalable and efficient access to the highly substituted pyrrolidines with a trifluoromethylated, all-carbon quaternary stereocenter in good yields with up to greater than 20:1 d.r. and 98 % ee. The reaction has a broad substrate scope and tolerates a wide range of functional groups.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, China.
authors.forename: Zhan-Ming
authors.initials: ZM
authors.lastname: Zhang
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, China.
authors.forename: Bing
authors.initials: B
authors.lastname: Xu
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, China.
authors.forename: Shan
authors.initials: S
authors.lastname: Xu
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, China.
authors.forename: Hai-Hong
authors.initials: HH
authors.lastname: Wu
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, China. jlzhang@chem.ecnu.edu.cn.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai, 200032, China. jlzhang@chem.ecnu.edu.cn.
authors.forename: Junliang
authors.initials: J
authors.lastname: Zhang
keywords: P,O ligand; azomethine ylides; copper; cycloaddition; heterocycles