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<p>We report a visible-light-driven asymmetric three-component reaction enabling direct enantioselective C2-functionalization of indoles. This method utilizes arylalkynes, benzoquinones, and indoles under chiral phosphoric acid catalysis to construct chiral indole derivatives bearing all-carbon quaternary stereocenters. The reaction proceeds via a cascade sequence: (1) Paternò-Büchi [2 + 2] cycloaddition between arylalkynes and benzoquinones, (2) electrocyclic ring-opening to generate <i>para</i>-quinone methide intermediates, and (3) enantioselective 1,6-addition of indoles at C2 to the <i>para</i>-quinone methide. This single-flask process forges three new bonds with high enantioselectivity. Importantly, exploiting the aldehyde functionality, products are readily transformed into conventionally inaccessible indoles with all-carbon quaternary stereocenters, highlighting the synthetic utility of this methodology.</p> Graphical abstract <p></p>

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Asymmetric C2-functionalization of indoles via visible-light-promoted three-component reaction

  • 期刊论文

  • 发表日期：

    2025年8月15日

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  • Han-Peng Pan,
  • Xiao-Ying Hu,
  • Jun-Hui Luo,
  • Zhao-Jie Fu,
  • Xin-Yi Yao,
  • Meng-Yan Ran,
  • Fang-Xin Wang,
  • Xiang-Zhi Zhang

摘要

We report a visible-light-driven asymmetric three-component reaction enabling direct enantioselective C2-functionalization of indoles. This method utilizes arylalkynes, benzoquinones, and indoles under chiral phosphoric acid catalysis to construct chiral indole derivatives bearing all-carbon quaternary stereocenters. The reaction proceeds via a cascade sequence: (1) Paternò-Büchi [2 + 2] cycloaddition between arylalkynes and benzoquinones, (2) electrocyclic ring-opening to generate para-quinone methide intermediates, and (3) enantioselective 1,6-addition of indoles at C2 to the para-quinone methide. This single-flask process forges three new bonds with high enantioselectivity. Importantly, exploiting the aldehyde functionality, products are readily transformed into conventionally inaccessible indoles with all-carbon quaternary stereocenters, highlighting the synthetic utility of this methodology.

Graphical abstract