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Enantioselective formal (3 + 3) cycloaddition of bicyclobutanes with nitrones enabled by asymmetric Lewis acid catalysis

Author

Listed:
  • Wen-Biao Wu

    (Hunan University
    Yangzhou University
    Hunan First Normal University)

  • Bing Xu

    (Fudan University)

  • Xue-Chun Yang

    (Hunan University)

  • Feng Wu

    (Hunan University)

  • Heng-Xian He

    (Hunan University)

  • Xu Zhang

    (Yangzhou University)

  • Jian-Jun Feng

    (Hunan University)

Abstract

The absence of catalytic asymmetric methods for synthesizing chiral (hetero)bicyclo[n.1.1]alkanes has hindered their application in new drug discovery. Here we demonstrate the achievability of an asymmetric polar cycloaddition of bicyclo[1.1.0]butane using a chiral Lewis acid catalyst and a bidentate chelating bicyclo[1.1.0]butane substrate, as exemplified by the current enantioselective formal (3 + 3) cycloaddition of bicyclo[1.1.0]butanes with nitrones. In addition to the diverse bicyclo[1.1.0]butanes incorporating an acyl imidazole group or an acyl pyrazole moiety, a wide array of nitrones are compatible with this Lewis acid catalysis, successfully assembling two congested quaternary carbon centers and a chiral aza-trisubstituted carbon center in the pharmaceutically important hetero-bicyclo[3.1.1]heptane product with up to 99% yield and >99% ee.

Suggested Citation

  • Wen-Biao Wu & Bing Xu & Xue-Chun Yang & Feng Wu & Heng-Xian He & Xu Zhang & Jian-Jun Feng, 2024. "Enantioselective formal (3 + 3) cycloaddition of bicyclobutanes with nitrones enabled by asymmetric Lewis acid catalysis," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52419-x
    DOI: 10.1038/s41467-024-52419-x
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    References listed on IDEAS

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    1. Kyle W. Quasdorf & Larry E. Overman, 2014. "Catalytic enantioselective synthesis of quaternary carbon stereocentres," Nature, Nature, vol. 516(7530), pages 181-191, December.
    2. Hai-Xia Wang & Chun Yang & Bai-Yu Xue & Ming-Sheng Xie & Yin Tian & Cheng Peng & Hai-Ming Guo, 2023. "Design of C1-symmetric tridentate ligands for enantioselective dearomative [3 + 2] annulation of indoles with aminocyclopropanes," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    3. Nils Frank & Jeremy Nugent & Bethany R. Shire & Helena D. Pickford & Patrick Rabe & Alistair J. Sterling & Tryfon Zarganes-Tzitzikas & Thomas Grimes & Amber L. Thompson & Russell C. Smith & Christophe, 2022. "Synthesis of meta-substituted arene bioisosteres from [3.1.1]propellane," Nature, Nature, vol. 611(7937), pages 721-726, November.
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