title: Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines.
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.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Aaron E
authors.initials: AE
authors.lastname: May
authors.forename: Patrick H
authors.initials: PH
authors.lastname: Willoughby
authors.forename: Thomas R
authors.initials: TR
authors.lastname: Hoye
mesh_terms: 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
chemical_list: D002264:Carboxylic Acids; D007454:Iodides; D010080:Oxazoles; D008094:Lithium