Citation: Feng Wu, Yuanjiu Xiao, Mengran Wei, Guoqiang Wang, Jian-Jun Feng. Lewis acid catalyzed enantioselective dearomative (3+2) cycloaddition of aromatic N-heterocycles with bicyclobutanes[J]. Chinese Chemical Letters, ;2026, 37(3): 111963. doi: 10.1016/j.cclet.2025.111963 shu

Lewis acid catalyzed enantioselective dearomative (3+2) cycloaddition of aromatic N-heterocycles with bicyclobutanes

Feng Wu ^{a, 1} ,
Yuanjiu Xiao ^{a, 1} ,
Mengran Wei ^{b, 1} ,
Guoqiang Wang ^{b, *,} ,
Jian-Jun Feng ^{a, *,}

a.
State Key Laboratory of Chemo and Biosensing, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
b.
State Key Laboratory of Coordination Chemistry, Key Laboratory of Mesoscopic Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China

wangguoqiang710@nju.edu.cn

jianjunfeng@hnu.edu.cn

Received Date: 10 June 2025
Revised Date: 2 October 2025
Accepted Date: 13 October 2025
Available Online: 14 October 2025

Figures(6)

Given the emerging demand to “escape from flatland” for modern medicinal chemistry, both the catalytic construction of complex three-dimensional molecular architectures from planar aromatics and the bioisosteric substitution of aromatic ring with bicyclo[2.1.1]hexanes (BCHs) become increasingly valuable. Despite notable advancements in the cycloaddition reactions involving bicyclo[1.1.0]butanes (BCBs) and 2π-components, the application of easily accessible aromatic compounds in these transformations, particularly in an asymmetric manner, is still relatively unexplored. Herein, we report a nickel-catalyzed enantioselective polar dearomative (3 + 2) cycloaddition of BCBs with benzazoles and indoles. This protocol offers an efficient route for the synthesis of N,S- or N,N-heterocycles decorated fused aza-BCHs bearing two quaternary carbon centers. This approach stands out for its practicality and appeal due to the utilization of easily accessible starting materials and catalysts, broad substrate scope, easy scalability, and the employment of mild reaction conditions. Density functional theory (DFT) calculations offer crucial insights into the reaction mechanism and elucidate the factors governing the enantioselectivity within the dearomative cycloaddition process.
- Bicyclo[1.1.0]butanes,
- Dearomatization,
- Cycloadditions,
- Bioisosteres,
- Asymmetric catalysis,
- Lewis acid
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