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

Yong Wang, Yanyan Li, Haohua Chen (), Yu Lan, Chao Pi, Yangjie Wu and Xiuling Cui ()
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Yong Wang: Zhengzhou University
Yanyan Li: Zhengzhou University
Haohua Chen: Henan Normal University
Yu Lan: Zhengzhou University
Chao Pi: Zhengzhou University
Yangjie Wu: Zhengzhou University
Xiuling Cui: Zhengzhou University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-50400-2

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