Cu-catalyzed skeletal rearrangement of O-propargylic electron-rich arylaldoximes into amidodienes

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16 Citations (Scopus)

Abstract

O-Propargylic oximes that possess an electron-rich p-(dimethylamino)phenyl group at the oxime moiety and an alkyl group at the propargylic position were efficiently converted in the presence of Cu(I) catalysts to the corresponding 1-amidodienes in good to excellent yields. The reaction proceeded via a 2,3-rearrangement, followed by isomerization of the resulting N-allenylnitrone to the amide, presumably through the oxaziridine intermediate.

Original languageEnglish
Pages (from-to)2562-2565
Number of pages4
JournalOrganic letters
Volume16
Issue number9
DOIs
Publication statusPublished - 2014 May 2

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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