NHC-Catalyzed and Brønsted Acid Copromoted E → Z Isomerization Mode of Breslow Intermediates Leading to Ralfuranones

Qingyun Wang, Xuyang Liang, Mingyi Pan, Yonggui Robin Chi, Pengcheng Zheng*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Different Z/E-isomers of functional molecules display distinct chemical and biological activities. The E → Z isomerization reaction is a contra-thermodynamic direction and presents a long-standing challenge in synthetic transformation. To date, organic catalysis methods for manipulating E/Z isomerization are still under development. Here we show a new N-heterocyclic carbene (NHC)-catalyzed E/Z isomerization mode. The E-isomer enedial undergoes E/Z isomerization to give a Z-isomer Breslow intermediate via NHC catalysis, and an intramolecular hydrogen bond can greatly stabilize this conformation. Subsequently, the Brønsted acid promotes the further redox-neutral reaction. The desired ralfuranone products obtained from our method can be readily transformed to various functional molecules.

Original languageEnglish
JournalOrganic Letters
DOIs
Publication statusAccepted/In press - 2025
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2025 American Chemical Society.

ASJC Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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