Synthesis of sugar oxazolines by intramolecular Ritter-like reaction of D-fructose precursors

Abstract

Treatment of D-fructopyranose and D-fructofuranosc 1,2-O-acetonide derivatives with triflic acid in the presence of a variety of nitriles results in the formation of fused or spiro 2-oxazolines. The reaction implies (i) activation of the anomeric centre with simultaneous isopropylidene cleavage, (ii) nucleophilic addition of the nitrile to the corresponding oxocarbenium cation intermediate and (iii) subsequent trapping of the resulting nitrilium ion species by the remaining hydroxyl group in an intramolecular Ritter-like reaction.