IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v15y2024i1d10.1038_s41467-024-52133-8.html
   My bibliography  Save this article

Simultaneous construction of inherent and axial chirality by cobalt-catalyzed enantioselective C-H activation of calix[4]arenes

Author

Listed:
  • Tong Li

    (Zhengzhou University)

  • Yanbo Zhang

    (Zhengzhou University)

  • Cong Du

    (Henan University)

  • Dandan Yang

    (Zhengzhou University)

  • Mao-Ping Song

    (Zhengzhou University)

  • Jun-Long Niu

    (Zhengzhou University)

Abstract

The simultaneous construction of multiple stereogenic elements in a single step is highly appealing and desirable in the field of asymmetric synthesis. Furthermore, the catalytic enantioselective synthesis of inherently chiral calix[n]arenes with high enantiopurity has long been a challenging endeavor. Herein, we report an enantioselective cobalt-catalyzed C–H activation/annulation for the efficient construction of inherently chiral calix[4]arenes bearing multiple C–N axially chiral element. By employing the benzamide tethered calix[4]arene as the substrate, the C–H annulation with alkynes can be successfully accomplished, leading to the generation of multiple stereogenic elements. A wide range of calix[4]arenes and alkynes are found to be well compatible, and exhibit good yields, high enantioselectivity and excellent diastereoselectivity. Notably, the gram-scale reaction, catalytic application, synthetic transformations, and chiral recognition further showcase the potential applications of this protocol.

Suggested Citation

  • Tong Li & Yanbo Zhang & Cong Du & Dandan Yang & Mao-Ping Song & Jun-Long Niu, 2024. "Simultaneous construction of inherent and axial chirality by cobalt-catalyzed enantioselective C-H activation of calix[4]arenes," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52133-8
    DOI: 10.1038/s41467-024-52133-8
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-024-52133-8
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-024-52133-8?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. Yishou Wang & Xiaohan Zhu & Deng Pan & Jierui Jing & Fen Wang & Ruijie Mi & Genping Huang & Xingwei Li, 2023. "Rhodium-catalyzed enantioselective and diastereodivergent access to diaxially chiral heterocycles," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    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. Chaochao Yao & Dan-Ran Li & Hua-Ming Xiang & Si-Jia Li & Yuepeng Lu & Zihao Wang & Tingrui Yin & Jiaqiang Wang & Kongling Feng & Cuiju Zhu & Hao Xu, 2024. "Copper-catalysed asymmetric annulation of yne-allylic esters with amines to access axially chiral arylpyrroles," Nature Communications, Nature, vol. 15(1), pages 1-10, 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_s41467-024-52133-8. 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.