Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines

Aaron E. May, Patrick H. Willoughby, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

(Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

Original languageEnglish (US)
Pages (from-to)3292-3294
Number of pages3
JournalJournal of Organic Chemistry
Volume73
Issue number8
DOIs
StatePublished - Apr 18 2008

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