Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines.
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.
May
Aaron E
AE
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Willoughby
Patrick H
PH
Hoye
Thomas R
TR
D000215:Acylation; D002264:Carboxylic Acids / Q000737:chemistry*; D003500:Cyclization; D007454:Iodides / Q000737:chemistry; D007536:Isomerism; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry
D002264:Carboxylic Acids; D007454:Iodides; D010080:Oxazoles; D008094:Lithium