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, Xiuling Cui

Abstract read

In one paragraph

Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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1 · What the graph read from it

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4 · The record

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5 · Who and what money

Authors and funding

7 authors.

Yong WangHenan Key Laboratory of Chemical Biology and Organic Chemistry, College of Chemistry, Zhengzhou University, Zhengzhou, Henan, PR China.ORCID http://orcid.org/0000-0002-8646-613X

Yanyan LiHenan Key Laboratory of Chemical Biology and Organic Chemistry, College of Chemistry, Zhengzhou University, Zhengzhou, Henan, PR China.

Haohua ChenState Key Laboratory of Antiviral Drugs, Henan Normal University, Xinxiang, Henan, PR China. chenhaohua@htu.edu.cn.ORCID http://orcid.org/0000-0001-7407-4326

Yu LanHenan Key Laboratory of Chemical Biology and Organic Chemistry, College of Chemistry, Zhengzhou University, Zhengzhou, Henan, PR China.ORCID http://orcid.org/0000-0002-2328-0020

Chao PiHenan Key Laboratory of Chemical Biology and Organic Chemistry, College of Chemistry, Zhengzhou University, Zhengzhou, Henan, PR China.

Yangjie WuHenan Key Laboratory of Chemical Biology and Organic Chemistry, College of Chemistry, Zhengzhou University, Zhengzhou, Henan, PR China.

Xiuling CuiHenan Key Laboratory of Chemical Biology and Organic Chemistry, College of Chemistry, Zhengzhou University, Zhengzhou, Henan, PR China. cuixl@zzu.edu.cn.ORCID http://orcid.org/0000-0001-5759-766X

Funding

Science and Technology Department of Henan Province (Henan Provincial Department of Science and Technology) 232102310366Science and Technology Department of Henan Province (Henan Provincial Department of Science and Technology) 242102310465

6 · The paper itself

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.

Identifiers

PMID39039050

DOI10.1038/s41467-024-50400-2

PMCPMC11263680

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