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<p>Molecular chirality is a cornerstone of modern chemistry and it has a profound impact on biological activity, chemical reactivity and physical property. Developing asymmetric synthesis methods to efficiently and precisely produce chiral molecules remains a challenging issue in organic chemistry. In recent years, transition-metal-catalyzed enantioselective C-H activation has emerged as an efficient strategy for the rapid access to valuable chiral compounds from readily available feedstocks in an atom- and step-economic manner. Here we report a rhodium(III)-catalyzed C-H activation/annulation of ketones with alkynes. This method features mild conditions, wide substrate scope, and perfect atom economy, affording a series of chiral tertiary indenols in excellent yields and enantioselectivity (up to 98% yield and 99% ee). Combined experimental and computational studies revealed the turnover-limiting step of the reaction and the origins of enantioselectivity and regioselectivity.</p>

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Enantioselective synthesis of indenols via rhodium(III)–catalyzed C-H activation/annulation of ketones with alkynes

  • 期刊论文

  • 发表日期：

    2025年2月12日

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  • Bo-Bo Gou,
  • Wen-Jie Shen,
  • Yuan-Jun Gao,
  • Qing Gu,
  • Shu-Li You

摘要

Molecular chirality is a cornerstone of modern chemistry and it has a profound impact on biological activity, chemical reactivity and physical property. Developing asymmetric synthesis methods to efficiently and precisely produce chiral molecules remains a challenging issue in organic chemistry. In recent years, transition-metal-catalyzed enantioselective C-H activation has emerged as an efficient strategy for the rapid access to valuable chiral compounds from readily available feedstocks in an atom- and step-economic manner. Here we report a rhodium(III)-catalyzed C-H activation/annulation of ketones with alkynes. This method features mild conditions, wide substrate scope, and perfect atom economy, affording a series of chiral tertiary indenols in excellent yields and enantioselectivity (up to 98% yield and 99% ee). Combined experimental and computational studies revealed the turnover-limiting step of the reaction and the origins of enantioselectivity and regioselectivity.