Exo-Cyclization: Intermolecular Methylene Transfer Sequence in Au-Catalyzed Reactions of O-Homopropargylic Oximes

Itaru Nakamura, Arinobu Hirayama, Shinya Gima, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

Abstract

The Au-catalyzed reactions of O-homopropaylic oximes afforded the 3-alkenylated isoxazolines in good to high yields. The mechanistic studies suggest that the reaction proceeds through an exo-cyclization followed by intermolecular methylene group transfer. In addition, oligomeric species of the starting material were observed in the reaction mixture by mass spectra, supporting our proposed mechanism, which proceeds through a repeated intermolecular C−C bond forming process.

Original languageEnglish
JournalChemistry - A European Journal
DOIs
Publication statusAccepted/In press - 2020

Keywords

  • alkynes
  • cascade reactions
  • gold catalysts
  • heterocycles
  • rearrangement

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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