Copper-Catalyzed\nAsymmetric Radical Oxysulfonylation\nof 2‑Vinylbenzoic Acids to Access Chiral Sulfonyl Phthalides

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

Publication Details

Journal
Figshare
Published
2024-11-07
DOI
https://doi.org/10.1021/acs.orglett.4c03530.s001
Primary Topic
Sulfur-Based Synthesis Techniques
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article
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article

Copper-Catalyzed\nAsymmetric Radical Oxysulfonylation\nof 2‑Vinylbenzoic Acids to Access Chiral Sulfonyl Phthalides

Figshare
Sulfur-Based Synthesis Techniques
article

Copper-Catalyzed\nAsymmetric Radical Oxysulfonylation\nof 2‑Vinylbenzoic Acids to Access Chiral Sulfonyl Phthalides

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Abstract

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

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Sulfur-Based Synthesis Techniques
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Copper-Catalyzed\nAsymmetric Radical Oxysulfonylation\nof 2‑Vinylbenzoic Acids to Access Chiral Sulfonyl Phthalides · Figshare (2024) | TGRS Research Map | TGRS