Citation: Fuxing Yang, Mengjie Gong, Yifei Zhang, Bangchi Wei, Nan Huang, Jun Jiang. Organocatalytic enantioselective construction of axially chiral phosphorodithiolated styrenes[J]. Chinese Chemical Letters, ;2026, 37(1): 111219. doi: 10.1016/j.cclet.2025.111219 shu

Organocatalytic enantioselective construction of axially chiral phosphorodithiolated styrenes

School of Chemistry and Chemical Engineering, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Guangxi University, Nanning 530004, China

huangnan0044@gxu.edu.cn

jiangjun@gxu.edu.cn

Received Date: 7 February 2025
Revised Date: 8 April 2025
Accepted Date: 15 April 2025
Available Online: 15 April 2025

Figures(6)

Albeit notable endeavors in the construction of organophosphorodithioates, the direct catalytic enantioselective synthesis of organophosphorodithioates still stands for a long-lasting challenge. Herein, an efficient organocatalytic enantioselective nucleophilic addition of vinylidene ortho-quinone methide with phosphinothioic thioanhydride as nucleophilic reagent has been achieved by the dual catalysis of cinchona alkaloid-derived squaramide and 4-dimethylaminopyridine. This protocol provides a straightforward approach for accessing a variety of axially chiral phosphorodithiolated styrenes in good yields (up to 98% yield) with high stereoselectivities (up to 97% ee and >99:1 E/Z).
- Phosphorodithiolated styrene,
- Axial chirality,
- Phosphinothioic thioanhydride,
- Vinylidene ortho-quinone methide,
- Dual catalysis
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