Copper-Catalyzed Asymmetric Radical Oxysulfonylation of 2-Vinylbenzoic Acids to Access Chiral Sulfonyl Phthalides

This study presents the development of a radical enantioselective alkene oxysulfonylation approach for the synthesis of enantioenriched sulfonyl phthalides via a catalyst system consisting of a copper salt and an OPPA ligand. The reaction proceeded under mild conditions with a wide range of substrates, good yields, and excellent enantioselectivities. Mechanistic studies suggested that the reaction proceeded through a radical-mediated process. Scalable synthesis and transformation experiments also demonstrated the applicable potential of this method.

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Publication Details

Journal
Organic Letters
Published
2024-11-07
DOI
https://doi.org/10.1021/acs.orglett.4c03530
Citations
2
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.50

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article

Copper-Catalyzed Asymmetric Radical Oxysulfonylation of 2-Vinylbenzoic Acids to Access Chiral Sulfonyl Phthalides

Xi-Tao Li, Xue-Juan Huang, Xiao-Cui Lan, Yuezhong Meng
2 citations
Organic Letters
Sulfur-Based Synthesis Techniques
0.50
article

Copper-Catalyzed Asymmetric Radical Oxysulfonylation of 2-Vinylbenzoic Acids to Access Chiral Sulfonyl Phthalides

Xi-Tao Li, Xue-Juan Huang, Xiao-Cui Lan, Yuezhong Meng
article en
2 citations

Abstract

This study presents the development of a radical enantioselective alkene oxysulfonylation approach for the synthesis of enantioenriched sulfonyl phthalides via a catalyst system consisting of a copper salt and an OPPA ligand. The reaction proceeded under mild conditions with a wide range of substrates, good yields, and excellent enantioselectivities. Mechanistic studies suggested that the reaction proceeded through a radical-mediated process. Scalable synthesis and transformation experiments also demonstrated the applicable potential of this method.

Organic LettersVol. 26(47)
Sun Yat-sen University (CN)
Science and Technology Foundation of Shenzhen City
Openalex Percentile: Top 38%
Sulfur-Based Synthesis Techniques
0.50
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