Dearomatization [4+2] cycloaddition for constructing bridged polycyclic lactams

This article presents a metal-free catalytic system for the [4+2] cycloaddition of isoquinoline and maleimide derivatives, enabling the one-step construction of structurally complex bridged polycyclic lactams. This three-component tandem cyclization reaction generates C-N, CO, and C-C bonds, achieving functionalization at the C1, N2, C3, and C4 positions of 3-halogenated isoquinolines. This dearomatization strategy exhibits exceptional chemoselectivity and regioselectivity, operates without transition metals, and offers a high atom and step economy.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc03128a
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Dearomatization [4+2] cycloaddition for constructing bridged polycyclic lactams

Zhongzhi Zhu, Tsz Woon Benedict Lo, Xiuwen Chen, Jingyi Chen et al.
Chemical Communications
Asymmetric Synthesis and Catalysis
article

Dearomatization [4+2] cycloaddition for constructing bridged polycyclic lactams

Zhongzhi Zhu, Tsz Woon Benedict Lo, Xiuwen Chen, Jingyi Chen, Shasha Wang, Jiaxin Liang, Qile Wu, Haoxian Wu
article en

Abstract

This article presents a metal-free catalytic system for the [4+2] cycloaddition of isoquinoline and maleimide derivatives, enabling the one-step construction of structurally complex bridged polycyclic lactams. This three-component tandem cyclization reaction generates C-N, CO, and C-C bonds, achieving functionalization at the C1, N2, C3, and C4 positions of 3-halogenated isoquinolines. This dearomatization strategy exhibits exceptional chemoselectivity and regioselectivity, operates without transition metals, and offers a high atom and step economy.

Chemical CommunicationsVol. 61(68)
Hong Kong Polytechnic University (HK), Wuyi University (CN), Wuyi University (CN)
National Natural Science Foundation of China, Department of Education of Guangdong Province
Openalex Percentile: Top 86%
Asymmetric Synthesis and Catalysis
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