Gold-Catalyzed Oxime-Oxime Rearrangement

Guven S., Ozer M. S., Kaya S., Menges N., BALCI M.

ORGANIC LETTERS, vol.17, no.11, pp.2660-2663, 2015 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 11
  • Publication Date: 2015
  • Doi Number: 10.1021/acs.orglett.5b01041
  • Journal Name: ORGANIC LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2660-2663
  • Middle East Technical University Affiliated: Yes

Abstract

The gold-catalyzed reaction of pyrrole and indole oximes having a propargyl group attached to the nitrogen atom was studied. The selective 6-endo-dig mode of cyclization was observed for the terminal alkynes giving rise to the formation of pyrazine N-oxides in the presence of a gold catalyst. However, the reaction with substituted alkyne transferred the oxime functionality intramolecularly from one carbon atom to another via the 7-endo-dig cyclization process. This transformation is unprecedented in the literature and is named an oximeoxime rearrangement.