Synthesis of sugar oxazolines by intramolecular Ritter-like reaction of D-fructose precursors
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...
| Autores: | , , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 2004 |
| País: | España |
| Recursos: | Universidad de Sevilla (US) |
| Repositório: | idUS. Depósito de Investigación de la Universidad de Sevilla |
| OAI Identifier: | oai:idus.us.es:11441/70422 |
| Acesso em linha: | https://hdl.handle.net/11441/70422 https://doi.org/10.1055/s-2004-830891 |
| Access Level: | Acceso aberto |
| Palavra-chave: | 2-oxazolines Carbohydrates Nitriles Ritter reaction Spiro compounds |
| Resumo: | 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. |
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