Enantioselective sulfonylation using sodium hydrogen sulfite, 4-substituted Hantzsch esters and 1-(arylethynyl)naphthalen-2-ols

Xinhua Wang; Qiuping Ding; Chenxi Yang; Jianguo Yang; Jie Wu

doi:10.1039/D2QO01654K

Enantioselective sulfonylation using sodium hydrogen sulfite, 4-substituted Hantzsch esters and 1-(arylethynyl)naphthalen-2-ols†

Xinhua Wang,^a Qiuping Ding,

^a Chenxi Yang,^b Jianguo Yang*^b and Jie Wu

*^bcd

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* Corresponding authors

^a College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang, China

^b School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, Taizhou, China
E-mail: jie_wu@fudan.edu.cn

^c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

^d School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

Abstract

Synthesis of sulfonyl-containing axially chiral styrenes through a catalytic asymmetric three-component reaction of 4-substituted Hantzsch esters, NaHSO₃ (sodium hydrogen sulfite), and 1-(arylethynyl)naphthalen-2-ols in the presence of a photocatalyst under visible light irradiation is reported. This transformation proceeds through a radical process under mild conditions, leading to axially chiral (S,E)-1-(1-(alkylsulfonyl)-2-arylvinyl)naphthalen-2-ols in good yields with excellent enantioselectivities. During the reaction process, excellent regioselectivity and chemoselectivity were observed as well. Notably, sodium hydrogen sulfite is used as the sulfur dioxide surrogate in this organocatalytic enantioselective radical sulfonylation under photoinduced conditions.

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DOI: https://doi.org/10.1039/D2QO01654K
Article type: Research Article
Submitted: 19 Oct 2022
Accepted: 10 Nov 2022
First published: 11 Nov 2022

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Org. Chem. Front., 2023,10, 92-98

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Enantioselective sulfonylation using sodium hydrogen sulfite, 4-substituted Hantzsch esters and 1-(arylethynyl)naphthalen-2-ols

X. Wang, Q. Ding, C. Yang, J. Yang and J. Wu, Org. Chem. Front., 2023, 10, 92 DOI: 10.1039/D2QO01654K

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Enantioselective sulfonylation using sodium hydrogen sulfite, 4-substituted Hantzsch esters and 1-(arylethynyl)naphthalen-2-ols†

Abstract

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Enantioselective sulfonylation using sodium hydrogen sulfite, 4-substituted Hantzsch esters and 1-(arylethynyl)naphthalen-2-ols

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