Copper-catalyzed tandem [2,3]-Rearrangement and 6π-3-Azatriene electrocyclization in (E) -O -Propargylic α,β-Unsaturated oximes

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Abstract

Cu-catalyzed cyclizations of (E)-O-propargylic oximes of α,β-unsaturated aldehydes were successfully carried out to afford the corresponding pyridine oxides in good to high yields. As an example, (E)-acrylaldehyde O-1,3-diphenylprop-2-ynyl oxime (1b) was reacted for 5 h in the presence of CuBr(PPh3)3 (10 mol %) and PPh3 (10 mol %) in DMSO at 120 C to afford 3-benzyl-2-phenylpyridine-N-oxide (2b) in 84% yield. In this case, the reaction proceeded via Cu-catalyzed propargyl oxime-allenyl nitrone rearrangement followed by 6-3-azatriene electrocyclization.

Original languageEnglish
Pages (from-to)7884-7886
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number23
DOIs
Publication statusPublished - 2010 Jun 16

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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