Nickel-Catalyzed Asymmetric Transfer Hydrogenation and α-Selective Deuteration ofN-Sulfonyl Imines with Alcohols: Access to α-Deuterated Chiral Amines

A nickel-catalyzed enantioselective transfer hydrogenation and deuteration of N -sulfonyl imines was developed. Excellent α-selectivity and high deuterium content were achieved by using inexpensive 2-propanol- d 8 as a deuterium source. As a highlight, no deuteration of β-C–H and the remote C–H of N -sulfonyl amines occurred, which is hard to achieve using other imines or by hydrogen isotope exchange with D 2 O. Mechanism studies indicated a stepwise pathway through the [Ni–D] intermediate.