Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones

Fo-Yun Lu; Yu-Jue Chen; Yuan Chen; Xuan Ding; Zhi Guan; Yan-Hong He

doi:10.1039/C9CC09178E

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Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones†

Fo-Yun Lu,‡^a Yu-Jue Chen,‡^a Yuan Chen,^a Xuan Ding,^a Zhi Guan

*^a and Yan-Hong He

*^a

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* Corresponding authors

^a Key Laboratory of Luminescent and Real-Time Analytical Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China
E-mail: guanzhi@swu.edu.cn, heyh@swu.edu.cn

Abstract

A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asymmetric proline-catalyzed alkylation in an undivided cell under constant-current conditions.

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DOI: https://doi.org/10.1039/C9CC09178E
Article type: Communication
Submitted: 26 Nov 2019
Accepted: 05 Dec 2019
First published: 06 Dec 2019

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Chem. Commun., 2020,56, 623-626

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Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones

F. Lu, Y. Chen, Y. Chen, X. Ding, Z. Guan and Y. He, Chem. Commun., 2020, 56, 623 DOI: 10.1039/C9CC09178E

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Chemical Communications

Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones†

Abstract

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Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones

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