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N-Heterocyclic carbene-catalyzed enantioselective synthesis of planar-chiral cyclophanes via dynamic kinetic resolution

Author

Listed:
  • Jiayan Li

    (Beijing Normal University)

  • Ziyang Dong

    (Beijing Normal University)

  • Yang Chen

    (Beijing University of Chemical Technology)

  • Zhanhui Yang

    (Beijing University of Chemical Technology)

  • Xinen Yan

    (Beijing Normal University)

  • Meng Wang

    (Beijing Normal University)

  • Chenyang Li

    (Beijing Normal University)

  • Changgui Zhao

    (Beijing Normal University)

Abstract

Planar-chiral cyclophanes have gained considerable concerns for drug discovery due to their unique conformational strain and 3D structure. However, the enantioselective synthesis of planar-chiral cyclophanes is a long-standing challenge for the synthetic community. We herein describe an N-heterocyclic carbene (NHC)-catalyzed asymmetric construction of planar-chiral cyclophanes. This transformation occurs through a dynamic kinetic resolution (DKR) process to convert racemic substrates into planar-chiral macrocycle scaffolds in good to high yields with high to excellent enantioselectivities. The ansa chain length and aromatic ring substituent size is crucial to achieve the DKR approach. Controlled experiments and DFT calculations were performed to clarify the DKR process.

Suggested Citation

  • Jiayan Li & Ziyang Dong & Yang Chen & Zhanhui Yang & Xinen Yan & Meng Wang & Chenyang Li & Changgui Zhao, 2024. "N-Heterocyclic carbene-catalyzed enantioselective synthesis of planar-chiral cyclophanes via dynamic kinetic resolution," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46376-8
    DOI: 10.1038/s41467-024-46376-8
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    References listed on IDEAS

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    1. Matthew N. Hopkinson & Christian Richter & Michael Schedler & Frank Glorius, 2014. "An overview of N-heterocyclic carbenes," Nature, Nature, vol. 510(7506), pages 485-496, June.
    2. Jia-Lei Yan & Rakesh Maiti & Shi-Chao Ren & Weiyi Tian & Tingting Li & Jun Xu & Bivas Mondal & Zhichao Jin & Yonggui Robin Chi, 2022. "Carbene-catalyzed atroposelective synthesis of axially chiral styrenes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
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