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Collective synthesis of acetylenic pharmaceuticals via enantioselective Nickel/Lewis acid-catalyzed propargylic alkylation

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  • Xihao Chang

    (University of Science and Technology of China)

  • Jiayin Zhang

    (University of Science and Technology of China)

  • Lingzi Peng

    (University of Science and Technology of China)

  • Chang Guo

    (University of Science and Technology of China)

Abstract

Chiral acetylenic derivatives are found in many bioactive compounds and are versatile functional groups in organic chemistry. Here, we describe an enantioselective nickel/Lewis acid-catalyzed asymmetric propargylic substitution reaction from simple achiral materials under mild condition. The introduction of a Lewis acid cocatalyst is crucial to the efficiency of the transformation. Notably, we investigate this asymmetric propargylic substitution reaction for the development of a range of structurally diverse natural products. The power of this strategy is highlighted by the collective synthesis of seven biologically active compounds: (−)-Thiohexital, (+)-Thiopental, (+)-Pentobarbital, (−)-AMG 837, (+)-Phenoxanol, (+)-Citralis, and (−)-Citralis Nitrile.

Suggested Citation

  • Xihao Chang & Jiayin Zhang & Lingzi Peng & Chang Guo, 2021. "Collective synthesis of acetylenic pharmaceuticals via enantioselective Nickel/Lewis acid-catalyzed propargylic alkylation," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-020-20644-9
    DOI: 10.1038/s41467-020-20644-9
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    Cited by:

    1. Xiang Pu & Qiu-Di Dang & Lei Yang & Xia Zhang & Dawen Niu, 2022. "Doubly stereoconvergent construction of vicinal all-carbon quaternary and tertiary stereocenters by Cu/Mg-catalyzed propargylic substitution," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Yulin Zhang & Yoshiaki Tanabe & Shogo Kuriyama & Ken Sakata & Yoshiaki Nishibayashi, 2023. "Interplay of diruthenium catalyst in controlling enantioselective propargylic substitution reactions with visible light-generated alkyl radicals," Nature Communications, Nature, vol. 14(1), pages 1-16, December.

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