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

Peng Yang*, Li Zhang, Kaiyue Fu, Yaxin Sun, Xiuhua Wang, Jieyu Yue, Yu Ma* and Bo Tang*

*College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, P. R. China, Email: yangpengsdnu.edu.cn, maysdnu.edu.cn, tangbsdnu.edu.cn

P. Yang, L. Zhang, K. Fu, Y. Sun, X. Wang, J. Yue, Y. Ma, B. Tang, Org. Lett., 2020, 22, 8278-8284.

DOI: 10.1021/acs.orglett.0c02921

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Abstract

A nickel-catalyzed enantioselective transfer hydrogenation of N-sulfonyl imines offers excellent α-selectivity. The use of inexpensive 2-propanol-d₈ as a deuterium source enables a deuteration with high deuterium content. In addition, 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.

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(S)-Binapine

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Key Words

reduction of imines, isopropanol

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ID: J54-Y2020