Copper-Catalyzed Hydroamination: Enantioselective Addition of Pyrazoles to Cyclopropenes
Minghao Wang, Julie Simon, Mengfei Xu, Stephanie A. Corio, Jennifer S. Hirschi, Vy M. Dong
Abstract
Chiral N -cyclopropyl pyrazoles and structurally related heterocycles are prepared using an earth-abundant copper catalyst under mild reaction conditions with high regio-, diastereo-, and enantiocontrol. The observed N 2:N 1 regioselectivity favors the more hindered nitrogen of the pyrazole. Experimental and DFT studies support a unique mechanism that features a five-centered aminocupration.
Topics & Concepts
ChemistryRegioselectivityHydroaminationEnantioselective synthesisPyrazoleCatalysisCopperOrganic chemistryCombinatorial chemistryMedicinal chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis