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Organocatalytic asymmetric synthesis of Si-stereogenic silacycles

Author

Listed:
  • Jung Tae Han

    (Max-Planck-Institut für Kohlenforschung
    Korea Institute of Science and Technology (KIST))

  • Nobuya Tsuji

    (Hokkaido University)

  • Hui Zhou

    (Max-Planck-Institut für Kohlenforschung)

  • Markus Leutzsch

    (Max-Planck-Institut für Kohlenforschung)

  • Benjamin List

    (Max-Planck-Institut für Kohlenforschung
    Hokkaido University)

Abstract

A strong and confined Brønsted acid catalyzed enantioselective cyclization of bis(methallyl)silanes provides enantioenriched Si-stereogenic silacycles. High enantioselectivities of up to 96.5:3.5 er were obtained for a range of bis(methallyl)silanes. NMR and ESI-MS studies reveal that the formation of a covalent adduct irreversibly inhibits turnover. Remarkably, we found that acetic acid as an additive promotes the collapse of this adduct, enabling full turnover. Experimental investigation and density functional theory (DFT) calculations were conducted to elucidate the origin of this phenomenon and the observed enantioselectivity.

Suggested Citation

  • Jung Tae Han & Nobuya Tsuji & Hui Zhou & Markus Leutzsch & Benjamin List, 2024. "Organocatalytic asymmetric synthesis of Si-stereogenic silacycles," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-49988-2
    DOI: 10.1038/s41467-024-49988-2
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    References listed on IDEAS

    as
    1. Xi-Chao Wang & Bo Li & Cheng-Wei Ju & Dongbing Zhao, 2022. "Nickel(0)-catalyzed divergent reactions of silacyclobutanes with internal alkynes," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    2. Shuyou Chen & Delong Mu & Pei-Lin Mai & Jie Ke & Yingzi Li & Chuan He, 2021. "Enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
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