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Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations

Author

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  • Shan Wang

    (Southern University of Science and Technology)

  • Jian-Xin Zhang

    (Southern University of Science and Technology)

  • Tian-Yi Zhang

    (Southern University of Science and Technology)

  • Huan Meng

    (Southern University of Science and Technology)

  • Bi-Hong Chen

    (Southern University of Science and Technology)

  • Wei Shu

    (Southern University of Science and Technology)

Abstract

Chiral aliphatic amine and alcohol derivatives are ubiquitous in pharmaceuticals, pesticides, natural products and fine chemicals, yet difficult to access due to the challenge to differentiate between the spatially and electronically similar alkyl groups. Herein, we report a nickel-catalyzed enantioselective hydroalkylation of acyl enamines and enol esters with alkyl halides to afford enantioenriched α-branched aliphatic acyl amines and esters in good yields with excellent levels of enantioselectivity. The operationally simple protocol provides a straightforward access to chiral secondary alkyl-substituted amine and secondary alkyl-substituted alcohol derivatives from simple starting materials with great functional group tolerance.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-22983-7
    DOI: 10.1038/s41467-021-22983-7
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    Cited by:

    1. Xiao-Xu Wang & Yuan-Tai Xu & Zhi-Lin Zhang & Xi Lu & Yao Fu, 2022. "NiH-catalysed proximal-selective hydroalkylation of unactivated alkenes and the ligand effects on regioselectivity," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    2. Qian Gao & Wei-Cheng Xu & Xuan Nie & Kang-Jie Bian & Hong-Rui Yuan & Wen Zhang & Bing-Bing Wu & Xi-Sheng Wang, 2024. "Regio‐ and enantioselective nickel-alkyl catalyzed hydroalkylation of alkynes," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    3. 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.
    4. Jiangtao Ren & Zheng Sun & Shuang Zhao & Jinyuan Huang & Yukun Wang & Cheng Zhang & Jinhai Huang & Chenhao Zhang & Ruipu Zhang & Zhihan Zhang & Xu Ji & Zhihui Shao, 2024. "Enantioselective synthesis of chiral α,α-dialkyl indoles and related azoles by cobalt-catalyzed hydroalkylation and regioselectivity switch," Nature Communications, Nature, vol. 15(1), pages 1-14, December.

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