Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes

Yan-Xin Zheng, Li-Gao Liu, Tian-Qi Hu, Xiao Li, Zhou Xu, Xin Hong (), Xin Lu, Bo Zhou and Long-Wu Ye ()
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Yan-Xin Zheng: Xiamen University
Li-Gao Liu: Zhejiang University
Tian-Qi Hu: Xiamen University
Xiao Li: Xiamen University
Zhou Xu: Xuzhou Medical University
Xin Hong: Xiamen University
Xin Lu: Xiamen University
Bo Zhou: Xiamen University
Long-Wu Ye: Xiamen University

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract The asymmetric Büchner reaction and related arene cyclopropanations represent one type of the powerful methods for enantioselective dearomatization. However, examples of asymmetric Büchner reactions via a non-diazo approach are quite scarce, and the related arene cyclopropanation based on alkynes has not been reported. Herein, we disclose an asymmetric Büchner reaction and the related arene cyclopropanation by copper-catalyzed controllable cyclization of N-propargyl ynamides via vinyl cation intermediates, leading to chiral tricycle-fused cycloheptatrienes and benzonorcaradienes in high yields and enantioselectivities. Importantly, this protocol represents an asymmetric arene cyclopropanation reaction of alkynes and an asymmetric Büchner reaction based on vinyl cations.

Date: 2024
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DOI: 10.1038/s41467-024-53605-7

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