Skeletal rearrangement of O-propargylic formaldoximes by a gold-catalyzed cyclization/intermolecular methylene transfer sequence

Itaru Nakamura, Shinya Gima, Yu Kudo, Masahiro Terada

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Abstract Skeletal rearrangement of O-propargylic formaldoximes, in the presence of gold catalysts, afforded 4-methylene-2-isoxazolines in good to excellent yields by an intermolecular methylene transfer. In addition, the cascade reaction with maleimide in the presence of a gold catalyst afforded isoxazole derivatives by cyclization/methylene transfer and a subsequent ene reaction, whereas that using a copper catalyst gave oxazepines through a 2,3-rearrangement. Au is not like Cu: Skeletal rearrangement of O-propargylic formaldoximes, in the presence of gold catalysts effectively afforded 4-methylene-2-isoxazolines by intermolecular methylene transfer. The cascade reaction in the presence of gold proceeds by cyclization/methylene transfer and a subsequent ene reaction, whereas with a copper catalyst it proceeds by a 2,3-rearrangement.

Original languageEnglish
Pages (from-to)7154-7157
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number24
DOIs
Publication statusPublished - 2015 Jun 1

Keywords

  • copper
  • gold
  • heterocycles
  • rearrangements
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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