Nickel-Catalyzed Asymmetric Transfer Hydrogenation and α-Selective Deuteration of<i>N</i>-Sulfonyl Imines with Alcohols: Access to α-Deuterated Chiral Amines
Peng Yang, Li Zhang, Kaiyue Fu, Yaxin Sun, Xiuhua Wang, Jieyu Yue, Yu Ma, Bo Tang
Abstract
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-d8 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 D2O. Mechanism studies indicated a stepwise pathway through the [Ni–D] intermediate.
Topics & Concepts
ChemistryCatalysisSulfonylDeuteriumNickelTransfer hydrogenationOrganic chemistryCombinatorial chemistryMedicinal chemistryRutheniumQuantum mechanicsPhysicsAlkylChemical Reactions and IsotopesAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis