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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
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    References listed on IDEAS

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    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.
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