IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v15y2024i1d10.1038_s41467-024-52419-x.html
   My bibliography  Save this article

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
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-024-52419-x
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-024-52419-x?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    References listed on IDEAS

    as
    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.
    Full references (including those not matched with items on IDEAS)

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Po-Kai Peng & Andrew Isho & Jeremy A. May, 2024. "Regio- and enantioselective synthesis of acyclic quaternary carbons via organocatalytic addition of organoborates to (Z)-Enediketones," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    2. Yonghong Liu & Zhixian Wu & Jing-Ran Shan & Huaipu Yan & Er-Jun Hao & Lei Shi, 2024. "Titanium catalyzed [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes with 1,3-dienes for efficient synthesis of stilbene bioisosteres," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    3. Zongbin Jia & Liang Cheng & Long Zhang & Sanzhong Luo, 2024. "Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    4. Ming-Ming Li & Tianze Zhang & Lei Cheng & Wei-Guo Xiao & Jin-Tao Ma & Li-Jun Xiao & Qi-Lin Zhou, 2023. "Ketone α-alkylation at the more-hindered site," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    5. Jiawen Wang & Faqian He & Xiaoyu Yang, 2021. "Asymmetric construction of acyclic quaternary stereocenters via direct enantioselective additions of α-alkynyl ketones to allenamides," Nature Communications, Nature, vol. 12(1), pages 1-12, December.
    6. Dongquan Zhang & Miaomiao Li & Jiajia Li & Aijun Lin & Hequan Yao, 2021. "Rhodium-catalyzed intermolecular enantioselective Alder–ene type reaction of cyclopentenes with silylacetylenes," Nature Communications, Nature, vol. 12(1), pages 1-7, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52419-x. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.