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Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates

Author

Listed:
  • Yao Zhang

    (Nanjing University)

  • Deyong Qiao

    (Nanjing University)

  • Mei Duan

    (Nanjing University)

  • You Wang

    (Nanjing University)

  • Shaolin Zhu

    (Nanjing University
    Henan Normal University)

Abstract

Chiral α-aminoboronic acids and their derivatives are generally useful as bioactive compounds and some have been approved as therapeutic agents. Here we report a NiH-catalysed asymmetric hydroamidation process that with a simple amino alcohol ligand can easily produce a wide range of highly enantioenriched α-aminoboronates from alkenyl boronates and dioxazolones under mild conditions. The reaction is proposed to proceed by an enantioselective hydrometallation followed by an inner-sphere nitrenoid transfer and C–N bond forming sequence. The synthetic utility of this transformation was demonstrated by the efficient synthesis of a current pharmaceutical agent, Vaborbactam.

Suggested Citation

  • Yao Zhang & Deyong Qiao & Mei Duan & You Wang & Shaolin Zhu, 2022. "Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-33411-9
    DOI: 10.1038/s41467-022-33411-9
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    References listed on IDEAS

    as
    1. Jia-Wang Wang & Yan Li & Wan Nie & Zhe Chang & Zi-An Yu & Yi-Fan Zhao & Xi Lu & Yao Fu, 2021. "Catalytic asymmetric reductive hydroalkylation of enamides and enecarbamates to chiral aliphatic amines," Nature Communications, Nature, vol. 12(1), pages 1-10, December.
    2. Xuzhong Shen & Xu Chen & Jieping Chen & Yufeng Sun & Zhaoyang Cheng & Zhan Lu, 2020. "Ligand-promoted cobalt-catalyzed radical hydroamination of alkenes," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    3. Yulong Zhang & Xianfeng Xu & Shaolin Zhu, 2019. "Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    4. Shan Wang & Jian-Xin Zhang & Tian-Yi Zhang & Huan Meng & Bi-Hong Chen & Wei Shu, 2021. "Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    5. Yumeng Xi & Senjie Ma & John F. Hartwig, 2020. "Catalytic asymmetric addition of an amine N–H bond across internal alkenes," Nature, Nature, vol. 588(7837), pages 254-260, December.
    6. Xiaoli Jiang & Bo Han & Yuhang Xue & Mei Duan & Zhuofan Gui & You Wang & Shaolin Zhu, 2021. "Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
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