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December 8, 2025Organic Letters2 citations

Copper-Catalyzed Regio- and Enantioselective Acylation of 1,3-Enynes

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JHJing HeWYWan Seok YoonJYJaesook Yun

Key Points

  • Products show high enantioselectivity, creating all-carbon quaternary centers without significant side reactions.
  • Achieves chemoselective reaction via an enantioenriched allenylcopper species from acyl fluorides and enynes.
  • Method utilizes a copper-oxygen-coordinated transition state for efficient synthesis and broad functional group tolerance.
  • The technique enables scalable asymmetric reactions; validating its importance for synthetic organic chemistry.

Abstract

This work discloses the first enantioselective copper-catalyzed acylation of 1,3-enynes with acyl fluorides. The reaction proceeds via an enantioenriched allenylcopper species that is chemoselectively generated from enynes in the presence of competing acyl fluorides. The resulting products bearing all-carbon quaternary centers are obtained with high enantioselectivity through a copper-oxygen-coordinated transition state. The method provides a practical and scalable strategy for asymmetric C-C bond formation with broad functional group tolerance.

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Cite This Study

He et al. (2025) studied this question.

synapsesocial.com/papers/694020d72d562116f28fa8c0https://doi.org/10.1021/acs.orglett.5c04611
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