Phthalimide-based-SSCF3 reagent for enantioselective dithiotrifluoromethylation

Wen-Chao Gao; Jianrong Liu; Xuefeng Jiang

doi:10.1039/D1QO00001B

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Phthalimide-based-SSCF₃ reagent for enantioselective dithiotrifluoromethylation†

Wen-Chao Gao,

‡^ab Jianrong Liu ‡^a and Xuefeng Jiang

*^ac

Author affiliations

* Corresponding authors

^a Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, P. R. China
E-mail: xfjiang@chem.ecnu.edu.cn

^b College of Biomedical Engineering, Taiyuan University of Technology, Taiyuan, P. R. China

^c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai, P. R. China

Abstract

An electrophilic phthalimide-based-SSCF₃ reagent was designed and prepared for straightforward SSCF₃ incorporation of diverse β-keto esters in natural products, pharmaceuticals and biological molecules. The asymmetric dithiotrifluoromethylation was achieved with a good to excellent enantioselectivity, catalyzed by a cinchona-alkaloid-based catalyst (DHQD)₂PHAL via an ammonium-hydrogen-bonded induction mode.

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Article information

DOI: https://doi.org/10.1039/D1QO00001B
Article type: Research Article
Submitted: 01 Jan 2021
Accepted: 21 Jan 2021
First published: 22 Jan 2021

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Org. Chem. Front., 2021,8, 1275-1279

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Phthalimide-based-SSCF₃ reagent for enantioselective dithiotrifluoromethylation

W. Gao, J. Liu and X. Jiang, Org. Chem. Front., 2021, 8, 1275 DOI: 10.1039/D1QO00001B

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