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Copper-catalysed asymmetric annulation of yne-allylic esters with amines to access axially chiral arylpyrroles

Author

Listed:
  • Chaochao Yao

    (Central China Normal University)

  • Dan-Ran Li

    (Central China Normal University)

  • Hua-Ming Xiang

    (Central China Normal University)

  • Si-Jia Li

    (Central China Normal University)

  • Yuepeng Lu

    (Central China Normal University)

  • Zihao Wang

    (Central China Normal University)

  • Tingrui Yin

    (Central China Normal University)

  • Jiaqiang Wang

    (Central China Normal University)

  • Kongling Feng

    (Central China Normal University)

  • Cuiju Zhu

    (Central China Normal University)

  • Hao Xu

    (Central China Normal University)

Abstract

The construction of atropisomers with 1,2-diaxes, while maintaining high enantiocontrol, presents a significant challenge due to the dynamic nature of steric hindrance at ortho-aryl substituents. Although various catalytic asymmetric methods have been developed for accessing axially chiral arylpyrroles, the synthesis of axially chiral arylpyrroles with 1,2-diaxes in a catalytic asymmetric manner has remained rare. Herein, the authors report the synthesis of diverse axially chiral arylpyrroles with 1,2-diaxes, and C–C and C–N axes through copper-catalysed asymmetirc [4 + 1] annulation of yne-allylic esters with arylamines via a remote stereocontrol strategy. This approach provides facile access to a broad range of heterobiaryl atropisomers (67 examples) in excellent enantioselectivities, each bearing one or two C–C/C–N axes, demonstrating its versatility and efficiency. The utility of this methodology is further highlighted by the transformation of the product into chiral phosphine ligand, and chiral thioureas for the use in asymmetric catalysis.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-50896-8
    DOI: 10.1038/s41467-024-50896-8
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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. 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.
    3. Kimberly T. Barrett & Anthony J. Metrano & Paul R. Rablen & Scott J. Miller, 2014. "Spontaneous transfer of chirality in an atropisomerically enriched two-axis system," Nature, Nature, vol. 509(7498), pages 71-75, May.
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