Citation: Fen-Ya Xiong, Su-Rui Pan, Bao-Cheng Wang, Yu-Jie Li, Konstantin Nikolaevich Gavrilov, Wen-Jing Xiao, Liang-Qiu Lu. Control of adjacent S(Ⅳ) and spiro stereocenters via Pd-catalyzed asymmetric (3+2) cyclization[J]. Chinese Chemical Letters, ;2026, 37(12): 112446. doi: 10.1016/j.cclet.2026.112446 shu

Control of adjacent S(Ⅳ) and spiro stereocenters via Pd-catalyzed asymmetric (3+2) cyclization

Fen-Ya Xiong ^a ,
Su-Rui Pan ^a ,
Bao-Cheng Wang ^a ,
Yu-Jie Li ^a ,
Konstantin Nikolaevich Gavrilov ^{b, *,} ,
Wen-Jing Xiao ^{a, c} ,
Liang-Qiu Lu ^{a, c, d, *,}

a.
Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China
b.
Department of Chemistry, Ryazan State University named for S. Yesenin, Ryazan 390000, Russia
c.
Wuhan Institute of Photochemistry and Technology, Wuhan 430082, China
d.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

rsu.chem@gmail.com

luliangqiu@ccnu.edu.cn

Received Date: 3 September 2025
Revised Date: 18 January 2026
Accepted Date: 22 January 2026
Available Online: 23 January 2026

Figures(5)

Donor-acceptor (D-A) cyclopropanes have been widely used in asymmetric (3+2) dipolar cyclizations with various acceptors. However, the enantioselective construction of ring systems bearing heteroatom stereocenters using 2π-components with two different heteroatoms remains a challenge due to their low reactivity and the difficulty in controlling heteroatom chirality. Here, we report a Pd-catalyzed asymmetric (3+2) cyclization of oxindole-derived vinylcyclopropanes, a subclass of D-A cyclopropanes, with sulfinylamines, providing a versatile platform for synthesizing oxindole scaffolds bearing adjacent S(Ⅳ) and spiro stereocenters. The resulting products demonstrate excellent stability and are promising precursors for cyclic sulfinamides through stereospecific transformations. In addition, control experiments and NMR analysis reveal the crucial role of hydrogen bonding in substrate activation and stereoinduction.
- Heteroatom chirality,
- Spiro stereocenter,
- Palladium catalysis,
- Asymmetric cyclization,
- D-A cyclopropane
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