Diastereo- and enantioselective copper(I)-catalyzed intermolecular [3+2] cycloaddition of azomethine ylides with β-trifluoromethyl β,β-disubstituted enones

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. Out on pyrrol(idine): An asymmetric [3+2] cycloaddition reaction of azomethine ylides with β-trifluoromethyl β,β-disubstituted enones is enabled by the copper(I) catalyst with Ming-Phos ligand. The highly substituted product pyrrolidines, having a trifluoromethylated, all-carbon quaternary stereocenter, are isolated in good yields with up to greater than 20:1 d.r. and 98 % ee.