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

1 Citation (Scopus)

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
Pages (from-to)15816-15820
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number68
DOIs
Publication statusPublished - 2020 Dec 4

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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