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<p>Enantioselective intramolecular radical difunctionalization of alkenes involving sulfur dioxide through a three-component reaction of 4-arylpent-4-enoic acids, sodium hydrogen sulfite and thianthrenium salts under copper catalysis and photocatalysis is reported, allowing the construction of chiral 5-((sulfonyl)methyl)dihydrofuran-2(3<i>H</i>)-ones with <i>β</i>-quaternary stereocenters. During the transformation, sodium hydrogen sulfite is used as the sulfur dioxide surrogate. Excellent enantiocontrol (up to 99% ee) and wide functional group compatibility are observed in this asymmetric radical sulfonylation.</p>

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Copper-catalyzed enantioselective radical sulfonylation from sodium hydrogen sulfite: construction of chiral sulfonated dihydrofuran-2(3H)-ones

  • 期刊论文

  • 发表日期：

    2025年8月6日

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  • Chenxin Wang,
  • Xinhua Wang,
  • Jiapian Huang,
  • Wei Xiao,
  • Min Yang,
  • Jie Wu

摘要

Enantioselective intramolecular radical difunctionalization of alkenes involving sulfur dioxide through a three-component reaction of 4-arylpent-4-enoic acids, sodium hydrogen sulfite and thianthrenium salts under copper catalysis and photocatalysis is reported, allowing the construction of chiral 5-((sulfonyl)methyl)dihydrofuran-2(3H)-ones with β-quaternary stereocenters. During the transformation, sodium hydrogen sulfite is used as the sulfur dioxide surrogate. Excellent enantiocontrol (up to 99% ee) and wide functional group compatibility are observed in this asymmetric radical sulfonylation.