Copper-Catalyzed Remote Asymmetric Three-Component Sulfonylation Using SO <sub>2</sub> as the Sulfur Source to Access Chiral Allylic Sulfones

A copper-catalyzed enantioselective sulfonylation of yne-allylic esters with sulfur dioxide and cyclopropan-1-ols is reported. This three-component reaction proceeds via selective ε-addition of γ-keto sulfinate to copper-allenylidene intermediates, enabling efficient synthesis of chiral allylic sulfones under mild conditions. The protocol features high enantioselectivity (up to 96% ee), broad functional group compatibility, and good yields.

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Publication Details

Journal
Organic Letters
Published
2026-05-19
DOI
https://doi.org/10.1021/acs.orglett.6c01600
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Copper-Catalyzed Remote Asymmetric Three-Component Sulfonylation Using SO 2 as the Sulfur Source to Access Chiral Allylic Sulfones

Xiang Ma, Huijing Xiang, Xingguang Li, Jiaxing Guo et al.
Organic Letters
Sulfur-Based Synthesis Techniques
article

Copper-Catalyzed Remote Asymmetric Three-Component Sulfonylation Using SO 2 as the Sulfur Source to Access Chiral Allylic Sulfones

Xiang Ma, Huijing Xiang, Xingguang Li, Jiaxing Guo, Jiale Li, Shuning Liu, Wenli Yan
article en

Abstract

A copper-catalyzed enantioselective sulfonylation of yne-allylic esters with sulfur dioxide and cyclopropan-1-ols is reported. This three-component reaction proceeds via selective ε-addition of γ-keto sulfinate to copper-allenylidene intermediates, enabling efficient synthesis of chiral allylic sulfones under mild conditions. The protocol features high enantioselectivity (up to 96% ee), broad functional group compatibility, and good yields.

Organic Letters
Shanghai University (CN), East China University of Science and Technology (CN), Institute of Molecular Functional Materials (CN)
Openalex Percentile: Top 8%
Sulfur-Based Synthesis Techniques
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Copper-Catalyzed Remote Asymmetric Three-Component Sulfonylation Using SO <sub>2</sub> as the Sulfur Source to Access Chiral Allylic Sulfones — Xiang Ma, Huijing Xiang, et al. · Organic Letters (2026) | TGRS Research Map | TGRS