Lewis acid-mediated reactions of alkyl azides with alpha,beta-unsaturated ketones.
[reaction: see text] Alkyl azides react with saturated ketones upon treatment with Lewis acids to afford ring-expansion products through the azido-Schmidt reaction, but this reaction does not proceed when alpha,beta-unsaturated ketones are used. In this study, alkyl azides were reacted with enones in the presence of Lewis acids to give enaminones (vinylogous amides), which formally involve a ring contraction reaction. The mechanism and scope of this reaction is discussed.
Reddy
D Srinivasa
DS
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Malott Hall, Room 4070, University of Kansas, Lawrence, Kansas 66045-7582, USA.
Judd
Weston R
WR
Aubé
Jeffrey
J
D000143:Acids / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure
D000143:Acids; D001386:Azides; D007659:Ketones