Cu(I)-Ming-phos Catalyzed Enantioselective [3+2] Cycloadditions of Glycine ketimines to β-Trifluoromethyl Enones

A catalytic asymmetric [3+2] cycloaddition of glycine ketimines with β-CF₃ β,β-disubstituted enones was realized in the presence of a chiral copper(I)/Ming-Phos complex. This method provides an access to construct highly functionalized pyrrolidines bearing three contiguous stereocenters, which including a trifluoromethylated all-carbon quaternary stereocenter. The features of this reaction include high chemo-, diastereo-, enantioselectivity (up to >20:1 cr, >20:1 dr, 98% ee), readily available starting materials, well functional-group tolerance and mild reaction conditions. Control experiments demonstrate that the fluoro-substituent is crucial for the reactivity. (Figure presented.).