The base-promoted reaction of a-azido ketones with aldehydes and ketones provides a new and simple route to either αpha;-azido-β-hydroxy ketones, which are valuable 1, 2, 3-trifunctionalized synthons, or 2, 5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction. The αpha;-azido-β-hydroxy ketones are formed by an aldol reaction between an enolate of the αpha;-azidoketone and an aldehyde. The 2, 5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the αpha;-azido ketone enolate.
ASJC Scopus subject areas
- Organic Chemistry