Gold-Catalyzed Oxime-Oxime Rearrangement
ORGANIC LETTERS, vol.17, no.11, pp.2660-2663, 2015 (SCI-Expanded, Scopus)
- 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.