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<p>Carboxylic ester motifs are prevalent in biological, chemical and materials sciences, and the asymmetric α-functionalization of simple esters plays a crucial role in the field of organic synthesis. Here we present a versatile electricity-driven asymmetric Lewis base catalysis strategy for the oxidative radical cross-coupling of simple esters with silyl enol ethers. This approach integrates the electrochemical anodic oxidation process with chiral isothiourea catalysis, enabling a polarity inversion at the nucleophilic carbon of the enolate to trigger the formation of a chiral isothiourea-bound α-carbonyl radical species from a C1-ammonium enolate. The combination of asymmetric Lewis base catalysis and electrochemistry unlocks mild oxidative radical coupling reactions, achieving up to 98% enantiomeric excess and demonstrating broad substrate compatibility. This work underscores the synthetic potential of the approach and provides a platform for advancing asymmetric electrosynthesis.</p><p></p>

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Enantioselective radical α-enolation of esters via electrochemical chiral isothiourea catalysis

  • 期刊论文

  • 发表日期：

    2025年9月8日

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  • Ning Li,
  • Xuzhen Ye,
  • Yong Liu,
  • Jin Song

摘要

Carboxylic ester motifs are prevalent in biological, chemical and materials sciences, and the asymmetric α-functionalization of simple esters plays a crucial role in the field of organic synthesis. Here we present a versatile electricity-driven asymmetric Lewis base catalysis strategy for the oxidative radical cross-coupling of simple esters with silyl enol ethers. This approach integrates the electrochemical anodic oxidation process with chiral isothiourea catalysis, enabling a polarity inversion at the nucleophilic carbon of the enolate to trigger the formation of a chiral isothiourea-bound α-carbonyl radical species from a C1-ammonium enolate. The combination of asymmetric Lewis base catalysis and electrochemistry unlocks mild oxidative radical coupling reactions, achieving up to 98% enantiomeric excess and demonstrating broad substrate compatibility. This work underscores the synthetic potential of the approach and provides a platform for advancing asymmetric electrosynthesis.