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Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles

Author

Listed:
  • Guodong Fan

    (Guizhou University)

  • Qingyun Wang

    (Guizhou University)

  • Jun Xu

    (Guizhou University of Traditional Chinese Medicine)

  • Pengcheng Zheng

    (Guizhou University)

  • Yonggui Robin Chi

    (Guizhou University
    Nanyang Technological University)

Abstract

A carbene-catalyzed chemoselective reaction of unsymmetric enedials is disclosed. The reaction provides a concise access to bicyclic furo[2,3-b]pyrroles derivatives in excellent selectivity. A main challenge in this reaction is chemoselective reaction of the two aldehyde moieties in the enedial substrates. Mechanistic studies via experiments suggest that our chemoselectivity controls are mostly achieved on the reducing properties of different sited Breslow intermediates. Several side reactions processes and the corresponding side adducts are also studied by high resolution mass spectroscopy analysis. Our method allows for efficient assembly of the furo[2,3-b]pyrrole structural moieties and their analogues widely found in natural products and pharmaceuticals.

Suggested Citation

  • Guodong Fan & Qingyun Wang & Jun Xu & Pengcheng Zheng & Yonggui Robin Chi, 2023. "Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-39988-z
    DOI: 10.1038/s41467-023-39988-z
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    References listed on IDEAS

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    1. Mattia Silvi & Paolo Melchiorre, 2018. "Enhancing the potential of enantioselective organocatalysis with light," Nature, Nature, vol. 554(7690), pages 41-49, February.
    2. Zhipeng Zhang & Han Yong Bae & Joyram Guin & Constantinos Rabalakos & Manuel van Gemmeren & Markus Leutzsch & Martin Klussmann & Benjamin List, 2016. "Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes," Nature Communications, Nature, vol. 7(1), pages 1-8, November.
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    Cited by:

    1. Shao-Qing Shi & Chen-Chang Cui & Lin-Lin Xu & Jin-Peng Zhang & Wen-Juan Hao & Jianyi Wang & Bo Jiang, 2024. "Enantioselective synthesis of saddle-shaped eight-membered lactones with inherent chirality via organocatalytic high-order annulation," Nature Communications, Nature, vol. 15(1), pages 1-11, December.

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