Citation: Dongyan Ju, Hui Wang, Chuang Zhao, Jiahang Li, Luoluo Li, Xiaoyan Liu, Jie Tao, Junliang Zhang, Jinbo Zhao. A facile entry toward multi-substituted chiral cyclic nitrones and N-heterocycles via Pd-catalyzed enantioselective cyclization coupling of alkenyl oxime[J]. Chinese Chemical Letters, ;2026, 37(7): 112000. doi: 10.1016/j.cclet.2025.112000 shu

A facile entry toward multi-substituted chiral cyclic nitrones and N-heterocycles via Pd-catalyzed enantioselective cyclization coupling of alkenyl oxime

Dongyan Ju ^a ,
Hui Wang ^a ,
Chuang Zhao ^a ,
Jiahang Li ^a ,
Luoluo Li ^a ,
Xiaoyan Liu ^a ,
Jie Tao ^a ,
Junliang Zhang ^{a, b, *,} ,
Jinbo Zhao ^{a, *,}

a.
College of Chemistry and Life Sciences, Changchun University of Technology, Changchun 130012, China
b.
Department of Chemistry, Fudan University, Shanghai 200433, China

junliangzhang@fudan.edu.cn

zhaojinbo@ccut.edu.cn

Received Date: 24 April 2025
Revised Date: 11 October 2025
Accepted Date: 21 October 2025
Available Online: 24 October 2025

Figures(5)

Multi-substituted pyrrolidine and piperidine N-heterocycles are the top scaffolds of clinical drugs, but syntheses of these scaffolds are far from trivial. Herein, we report a highly enantioselective protocol for the synthesis of 5- and 6-membered cyclic nitrones via Pd-catalyzed cyclization coupling of alkenyl oximes with aryl, alkenyl and alkynyl (pseudo)halides enabled by chiral sulfonamidephosphine (SadPhos) ligands. These cyclic nitrones products, besides their significance per ser, can be facilely converted to multi-substituted pyrrolidines and piperidines by simple operations. This study also represents the first example of two-component catalytic asymmetric synthesis of cyclic nitrones and provides important insights for further development of enantioselective heterocyclization reaction and processes involving multiple selectivity issues.
- Palladium,
- N-Heterocycle,
- Nitrone,
- Oxime,
- Cyclization
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