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Catalytic Asymmetric Imine Cross-Coupling Reaction

  • Xiang-Lei Han
    Xiang-Lei Han
    Department of Chemistry, Zhejiang University, Hangzhou 310027, China
    Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou 310030, China
  • Bin Hu
    Bin Hu
    Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, United States
    More by Bin Hu
  • Chao Fei
    Chao Fei
    Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, United States
    More by Chao Fei
  • Zhe Li
    Zhe Li
    Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, United States
    More by Zhe Li
  • Yang Yu
    Yang Yu
    Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou 310030, China
    More by Yang Yu
  • Cheng Cheng
    Cheng Cheng
    Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou 310030, China
    More by Cheng Cheng
  • Bruce Foxman
    Bruce Foxman
    Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, United States
    More by Bruce Foxman
  • Jisheng Luo*
    Jisheng Luo
    Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou 310030, China
    *[email protected]
    More by Jisheng Luo
  • , and 
  • Li Deng*
    Li Deng
    Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou 310030, China
    *[email protected]
    More by Li Deng
Cite this: J. Am. Chem. Soc. 2023, 145, 8, 4400–4407
Publication Date (Web):February 17, 2023
https://doi.org/10.1021/jacs.3c00051
Copyright © 2023 American Chemical Society

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    Abstract

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    Catalytic asymmetric cross-coupling of imines constitutes a particularly desirable method for the synthesis of chiral vicinal diamines directly from readily available achiral precursors. The potential of this method lies in the possibility of utilizing a variety of imines as reacting partners. However, the realization of highly stereoselective cross-coupling of two different imines proved to be a formidable challenge. Herein we report an unprecedented catalytic asymmetric cross-coupling reaction that tolerates a variety of ketimines and aldimines as nucleophiles and electrophiles, respectively. The realization of this reaction resulted from the development of a new chiral ammonium catalyst, which was guided by insights from studies of catalyst–substrate interactions. With a 0.5 mol % loading of an organocatalyst, this reaction proceeded in a highly diastereo- and enantioselective manner to afford a diverse range of chiral vicinal diamines as nearly single stereoisomers. This catalytic reaction establishes a new approach for the asymmetric synthesis of chiral vicinal diamines.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.3c00051.

    • Experimental procedures and analysis data for all new compounds (PDF)

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    CCDC 2141554 and 2218458 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax: +44 1223 336033.

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    Cited By

    This article is cited by 5 publications.

    1. Yuhong Gao, Yiqun Zeng, Tianran Deng, Yu Deng, Cheng Cheng, Jisheng Luo, Li Deng. Catalytic Asymmetric Synthesis of Chiral α,α-Dialkyl Aminonitriles via Reaction of Cyanoketimines. Journal of the American Chemical Society 2024, 146 (18) , 12329-12337. https://doi.org/10.1021/jacs.4c03333
    2. Zhiyong Chi, Jia-Bin Liao, Xiuliang Cheng, Ziqi Ye, Wei Yuan, Yu-Mei Lin, Lei Gong. Asymmetric Cross-Coupling of Aldehydes with Diverse Carbonyl or Iminyl Compounds by Photoredox-Mediated Cobalt Catalysis. Journal of the American Chemical Society 2024, 146 (15) , 10857-10867. https://doi.org/10.1021/jacs.4c01443
    3. Cheng Cheng, Yang Yu, Yuhong Gao, Yi-Pan Li, Xiang-Lei Han, Jisheng Luo, Li Deng. Catalytic Asymmetric Construction of Chiral Amines with Three Nonadjacent Stereocenters via Trifunctional Catalysis. Journal of the American Chemical Society 2024, 146 (13) , 9356-9364. https://doi.org/10.1021/jacs.4c01671
    4. Junjie Yang, Yabin Zhang, Hong-Chai Fabio Wong, Jingxian Huang, Ying-Lung Steve Tse, Ying-Yeung Yeung. Design and Applications of Cyclopropenium Chalcogen Dihalides in Catalysis via C(sp3)–H···X Interactions. ACS Catalysis 2024, 14 (5) , 3018-3027. https://doi.org/10.1021/acscatal.4c00087
    5. Jiaxiang Lu, Zhenghua Li, Li Deng. Deoxygenative Nucleophilic Phosphonation and Electrophilic Alkylation of Secondary Amides: A Facile Access to Quaternary α-Aminophosphonates. Journal of the American Chemical Society 2024, 146 (7) , 4357-4362. https://doi.org/10.1021/jacs.3c14517