Chiral phosphoric acid-catalyzed enantioselective [5+1] cycloaddition reaction of C,N-cyclic azomethine imines with isocyanides

Jiulong Yu; Jinyu Wu; Yu Zhu; Dong Xiong; Lin Yang; Jun Li; Jianfeng Zheng

doi:10.1039/D3CC05890E

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Chiral phosphoric acid-catalyzed enantioselective [5+1] cycloaddition reaction of C,N-cyclic azomethine imines with isocyanides†

Jiulong Yu,‡^a Jinyu Wu,‡^a Yu Zhu,^a Dong Xiong,^a Lin Yang,^a Jun Li

*^b and Jianfeng Zheng

*^a

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* Corresponding authors

^a School of Chemistry, Southwest Jiaotong University, Chengdu 610031, China
E-mail: jfzheng@swjtu.edu.cn

^b Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, Jinhua, China
E-mail: jun_li@zjnu.edu.cn

Abstract

The first catalytic enantioselective [5+1] cycloaddition reactions of C,N-cyclic azomethine imines with isocyanides are reported herein. The method displays a broad substrate scope and atom-economy. A series of chiral tetrahydroisoquinoline containing indole skeletons were obtained in up to 90% yield with 95% ee under mild reaction conditions. A possible catalytic model was also proposed.

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DOI: https://doi.org/10.1039/D3CC05890E
Article type: Communication
Submitted: 02 Dec 2023
Accepted: 04 Feb 2024
First published: 06 Feb 2024

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Chem. Commun., 2024,60, 2637-2640

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Chiral phosphoric acid-catalyzed enantioselective [5+1] cycloaddition reaction of C,N-cyclic azomethine imines with isocyanides

J. Yu, J. Wu, Y. Zhu, D. Xiong, L. Yang, J. Li and J. Zheng, Chem. Commun., 2024, 60, 2637 DOI: 10.1039/D3CC05890E

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Chemical Communications

Chiral phosphoric acid-catalyzed enantioselective [5+1] cycloaddition reaction of C,N-cyclic azomethine imines with isocyanides†

Abstract

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Chiral phosphoric acid-catalyzed enantioselective [5+1] cycloaddition reaction of C,N-cyclic azomethine imines with isocyanides

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