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A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids

Opened Access A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids

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Autor: Ros Lao, Abel
Álvarez González, Eleuterio
Dietrich, Hansjörg
Batarda Fernandes, Rosario
Lassaletta Simón, José María
Departamento: Universidad de Sevilla. Departamento de Química Orgánica
Fecha: 2005
Publicado en: Synlett, 19, 2899-2904.
Tipo de documento: Artículo
Resumen: The 1,3-dipolar cycloaddition of a variety of aromatic and aliphatic nitrile oxides to 2,5-trans-2,5-diphenylpyrrolidine derived acrylamide and cinnamamide efficiently affords the corresponding 4,5-dihydroisoxazole-5- carboxamides in a highly regio- and stereoselective manner. The cycloaddition of aliphatic nitrile oxides to the analogue methacrylamide proceeds also smoothly to afford the expected cycloadducts in moderate yields and very high regio- and stereoselectivity. In sharp contrast, aromatic nitrile oxides react with the same amide to afford 5-methyl-4,5-dihydroisoxazole-5-carboxamides in higher yields but as near 1:1 mixtures of diastereoisomers. Acid hydrolysis of these products afforded enantiopure 4,5-dihydroisoxazole-5-carboxylic acids. © Georg Thieme Verlag Stuttgart.
Cita: Ros Lao, A., Álvarez González, E., Dietrich, H., Batarda Fernandes, R. y Lassaletta Simón, J.M. (2005). A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids. Synlett, 19, 2899-2904.
Tamaño: 177.5Kb
Formato: PDF

URI: https://hdl.handle.net/11441/70420

DOI: 10.1055/s-2005-921894

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