Reversal of Enantioselectivity in the Conjugate Addition Reaction of Cyclic Enones with the CuOTf/Azolium Catalytic System.

Hydroxyamide-functionalized azolium salt (NHC•HI ) was evaluated for dual enantioselective control in a Cu-catalyzed asymmetric conjugate addition (ACA) reaction. This investigation was based on our previously reported ACA reaction catalyzed using CuOTf combined with NHC•AgI complex . It was revealed that the stereocontrol of the catalytic ACA reaction depended on the order of the addition of the substrates.