Chiral Trifluoromethylated Pyrrolidines via Cu–Catalyzed Asymmetric 1,3‐Dipolar Cycloaddition
Xiang Cheng, Dingce Yan, Xiu‐Qin Dong, Chun‐Jiang Wang
Abstract
Abstract An efficient access to chiral pyrrolidine derivatives bearing one trifluoromethylated quaternary stereogenic centers is developed through Cu(I)/( S )‐TF‐BiphamPhos‐catalyzed asymmetric 1,3‐dipolar cycloaddition of azomethine ylides with tert ‐butyl 2‐(trifluoromethyl)acrylate in moderate to high yields, excellent diastereoselectivities and good enantioselectivities (up to 95% yield, >20 : 1 dr, 89% ee).
Topics & Concepts
StereocenterChemistryPyrrolidineCycloadditionCatalysisEnantioselective synthesisTrifluoromethyl1,3-Dipolar cycloadditionYield (engineering)Medicinal chemistryAcrylateStereochemistryOrganic chemistryCombinatorial chemistryMonomerPolymerAlkylMaterials scienceMetallurgyFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods