Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines
Aaron E May1, Patrick H Willoughby, Thomas R Hoye
1Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Abstract:
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 degrees C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.
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