Base-Promoted Reactions of a-Azido Ketones with Aldehydes and Ketones: A Novel Entry to αpha;-Azido-β-hydroxy Ketones and 2, 5-Dihydro-5-hydroxyoxazoles

Tamas Patonay, Robert V. Hoffman

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2368-2377
Number of pages10
JournalJournal of Organic Chemistry
Volume60
Issue number8
DOIs
Publication statusPublished - Apr 1 1995

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Base-Promoted Reactions of a-Azido Ketones with Aldehydes and Ketones: A Novel Entry to αpha;-Azido-β-hydroxy Ketones and 2, 5-Dihydro-5-hydroxyoxazoles'. Together they form a unique fingerprint.

  • Cite this