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Enantioselective de novo construction of 3‑oxindoles via organocatalyzed formal [3 + 2] annulation from simple arylamines

Author

Listed:
  • Yong Wang

    (Zhengzhou University)

  • Yanyan Li

    (Zhengzhou University)

  • Haohua Chen

    (Henan Normal University
    Pingyuan Laboratory)

  • Yu Lan

    (Zhengzhou University
    Pingyuan Laboratory)

  • Chao Pi

    (Zhengzhou University
    Pingyuan Laboratory)

  • Yangjie Wu

    (Zhengzhou University
    Pingyuan Laboratory)

  • Xiuling Cui

    (Zhengzhou University
    Pingyuan Laboratory)

Abstract

The de novo construction of enantioenriched 3-hydroxyindolenines and 3-oxindoles from easily available starting materials has been highly desired. Herein, an enantioselectively intermolecular direct [3 + 2] annulation of aryl amine with 2,3-diketoesters to construct 3-hydroxyindolenines with a chiral tertiary alcohol has been disclosed. The results of control experiments and DFT calculation revealed that π − π interaction plays a pivotal role in the enantioselectivity-determining process of [3 + 2] annulation. The following unusual concerted [1,2]-ester migration provides a family of chiral 3-oxindoles in good to excellent yields with excellent enantioselectivity.

Suggested Citation

  • Yong Wang & Yanyan Li & Haohua Chen & Yu Lan & Chao Pi & Yangjie Wu & Xiuling Cui, 2024. "Enantioselective de novo construction of 3‑oxindoles via organocatalyzed formal [3 + 2] annulation from simple arylamines," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-50400-2
    DOI: 10.1038/s41467-024-50400-2
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