Diastereo- and Enantioselective Copper(I)-Catalyzed Intermolecular [3+2] Cycloaddition of Azomethine Ylides with β-Trifluoromethyl β,β-Disubstituted Enones

Zhan-Ming Zhang; Bing Xu; Shan Xu; Hai-Hong Wu; Junliang Zhang

doi:10.1002/anie.201602542

Diastereo- and Enantioselective Copper(I)-Catalyzed Intermolecular [3+2] Cycloaddition of Azomethine Ylides with β-Trifluoromethyl β,β-Disubstituted Enones

Angew Chem Int Ed Engl. 2016 May 17;55(21):6324-8. doi: 10.1002/anie.201602542. Epub 2016 Apr 13.

Authors

Zhan-Ming Zhang¹, Bing Xu¹, Shan Xu¹, Hai-Hong Wu¹, Junliang Zhang^{2

3}

Affiliations

¹ 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.
² 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.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai, 200032, China. jlzhang@chem.ecnu.edu.cn.

PMID: 27073118
DOI: 10.1002/anie.201602542

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.

Keywords: P,O ligand; azomethine ylides; copper; cycloaddition; heterocycles.

Publication types

Research Support, Non-U.S. Gov't