IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v14y2023i1d10.1038_s41467-023-40491-8.html
   My bibliography  Save this article

Diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis

Author

Listed:
  • Lei Dai

    (National University of Singapore)

  • Xueting Zhou

    (National University of Singapore
    International Campus of Tianjin University)

  • Jiami Guo

    (National University of Singapore
    International Campus of Tianjin University)

  • Xuan Dai

    (National University of Singapore)

  • Qingqin Huang

    (National University of Singapore
    International Campus of Tianjin University)

  • Yixin Lu

    (National University of Singapore
    International Campus of Tianjin University)

Abstract

The C−N axially chiral N-arylpyrrole motifs are privileged scaffolds in numerous biologically active molecules and natural products, as well as in chiral ligands/catalysts. Asymmetric synthesis of N-arylpyrroles, however, is still challenging, and the simultaneous creation of contiguous C−N axial and central chirality remains unknown. Herein, a diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis has been developed. The key transformation is a one-pot, three-component oxo-diarylation reaction, which simultaneously creates a C−N axial chirality and a central quaternary stereogenic center. A broad range of unactivated alkynes were readily employed as a reaction partner in this transformation, and the N-arylpyrrole products are obtained in good yields, with excellent enantioselectivities and very good diastereoselectivities. Notably, the N-arylpyrrole skeletons represent interesting structural motifs that could be used as chiral ligands and catalysts in asymmetric catalysis.

Suggested Citation

  • Lei Dai & Xueting Zhou & Jiami Guo & Xuan Dai & Qingqin Huang & Yixin Lu, 2023. "Diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-40491-8
    DOI: 10.1038/s41467-023-40491-8
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-023-40491-8
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-023-40491-8?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. Lei Zhang & Shao-Hua Xiang & Jun (Joelle) Wang & Jian Xiao & Jun-Qi Wang & Bin Tan, 2019. "Phosphoric acid-catalyzed atroposelective construction of axially chiral arylpyrroles," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    2. Changgui Zhao & Donghui Guo & Kristin Munkerup & Kuo-Wei Huang & Fangyi Li & Jian Wang, 2018. "Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes," Nature Communications, Nature, vol. 9(1), pages 1-10, December.
    3. Sheng-Cai Zheng & San Wu & Qinghai Zhou & Lung Wa Chung & Liu Ye & Bin Tan, 2017. "Erratum: Organocatalytic atroposelective synthesis of axially chiral styrenes," Nature Communications, Nature, vol. 8(1), pages 1-1, December.
    4. Shengnan Jin & Jinxia Li & Kang Liu & Wei-Yi Ding & Shuai Wang & Xiujuan Huang & Xue Li & Peiyuan Yu & Qiuling Song, 2022. "Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    5. Sheng-Cai Zheng & San Wu & Qinghai Zhou & Lung Wa Chung & Liu Ye & Bin Tan, 2017. "Organocatalytic atroposelective synthesis of axially chiral styrenes," Nature Communications, Nature, vol. 8(1), pages 1-9, August.
    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. Jie Wang & Jun Gu & Jia-Yu Zou & Meng-Jie Zhang & Rui Shen & Zhiwen Ye & Ping-Xun Xu & Ying He, 2024. "Photocatalytic Z/E isomerization unlocking the stereodivergent construction of axially chiral alkene frameworks," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    2. Zhouli Hu & Chenlong Wei & Qianqian Shi & Xianfang Hong & Jinhua Liu & Xiangui Zhou & Jinna Han & Wei Cao & Ashis Kumar Gupta & Xiaoxiang Zhang & Donghui Wei & Zhenqian Fu & Wei Huang, 2022. "Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    3. Heng Wang & Xiaofeng Jie & Qinglei Chong & Fanke Meng, 2024. "Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    4. Shanglin Chen & Ya-Nan Wang & Jinhui Xie & Wangyang Li & Mingxing Ye & Xingxing Ma & Kai Yang & Shijun Li & Yu Lan & Qiuling Song, 2024. "Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions," Nature Communications, Nature, vol. 15(1), pages 1-14, 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:14:y:2023:i:1:d:10.1038_s41467-023-40491-8. 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.