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Synlett 2004(12): 2230-2232
DOI: 10.1055/s-2004-830891
DOI: 10.1055/s-2004-830891
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Sugar Oxazolines by Intramolecular Ritter-Like Reaction of d-Fructose Precursors
Further Information
Received
20 May 2004
Publication Date:
04 August 2004 (online)
Publication History
Publication Date:
04 August 2004 (online)
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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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References
The notation of atoms for NMR data has been kept consistent with that of the parent d-fructose precursor.