Nickel-Catalyzed Chemo- and Enantioselective Hydrogenation and Deuteration of α,β-Unsaturated Ketimines Using Alcohols: Synthesis of Deuterated Chiral Allylic Amines

Li Zhang, Yuting Zhu, Ping Li*, Peng Yang*, Bo Tang*

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

L. Zhang, Y. Zhu, P. Li, P. Yang, B. Tang, Org. Lett., 2023, 25, 8739-8744.

DOI: 10.1021/acs.orglett.3c03650

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Abstract

A nickel-catalyzed chemoselective asymmetric transfer hydrogenation of α,β-unsaturated ketimines using ethanol as a hydrogen donor provides chiral allylic amines under mild conditions. With this catalyst, C1-selective deuterated chiral allylic amines were efficiently synthesized using only stoichiometric 2-propanol-d₈.

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Key Words

reduction of imines, ethanol

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ID: J54-Y2023