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Cobalt(III)-catalyzed asymmetric ring-opening of 7-oxabenzonorbornadienes via indole C–H functionalization

Author

Listed:
  • Yang Zheng

    (Chinese Academy of Sciences)

  • Wen-Yun Zhang

    (Chinese Academy of Sciences)

  • Qing Gu

    (Chinese Academy of Sciences)

  • Chao Zheng

    (Chinese Academy of Sciences)

  • Shu-Li You

    (Chinese Academy of Sciences)

Abstract

Asymmetric ring-opening of 7-oxabenzonorbornadienes is achieved via Co-catalyzed indole C–H functionalization. The utilization of chiral Co-catalyst consisting of a binaphthyl-derived trisubstituted cyclopentadienyl ligand resulted in high yields (up to 99%) and excellent enantioselectivity (>99% ee) for the target products with tolerance for diverse functional groups. Opposite diastereoselectivities are obtained with chiral Co-catalyst or Cp*CoI2CO. Combined experimental and computational studies suggest β-oxygen elimination being the selectivity-determining step of the reaction. Meanwhile, the reactions of 7-azabenzonorbornadiene could also be executed in a diastereodivergent manner.

Suggested Citation

  • Yang Zheng & Wen-Yun Zhang & Qing Gu & Chao Zheng & Shu-Li You, 2023. "Cobalt(III)-catalyzed asymmetric ring-opening of 7-oxabenzonorbornadienes via indole C–H functionalization," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-36723-6
    DOI: 10.1038/s41467-023-36723-6
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    References listed on IDEAS

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    1. Tiffany Piou & Tomislav Rovis, 2015. "Rhodium-catalysed syn-carboamination of alkenes via a transient directing group," Nature, Nature, vol. 527(7576), pages 86-90, November.
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