Synthesis of Sugar Oxazolines by Intramolecular Ritter-Like Reaction of d-Fructose Precursors

José L. Jiménez Blanco; Enrique M. Rubio; Carmen Ortiz Mellet; José M. García Fernández

doi:10.1055/s-2004-830891

LETTER

Synthesis of Sugar Oxazolines by Intramolecular Ritter-Like Reaction of d-Fructose Precursors

José L. Jiménez Blanco^a, Enrique M. Rubio^b, Carmen Ortiz Mellet*^a, José M. García Fernández*^b
^a Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Aptdo. 553, 41071 Sevilla, Spain
Fax: +34(954)624960; e-Mail: mellet@us.es;
^b Instituto de Investigaciones Químicas, CSIC, Américo Vespucio 49, Isla de la Cartuja, 41092 Sevilla, Spain
Fax: +34(954)460565; e-Mail: jogarcia@iiq.csic.es;

Abstract

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Abstract

Treatment of d-fructopyranose and d-fructofuranose 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.

Key words

carbohydrates - nitriles - 2-oxazolines - spiro compounds - Ritter reaction

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The notation of atoms for NMR data has been kept consistent with that of the parent d-fructose precursor.