Artículo
A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids
Autor/es | Ros Lao, Abel
Álvarez González, Eleuterio Dietrich, Hansjörg Batarda Fernandes, Rosario Lassaletta Simón, José María |
Departamento | Universidad de Sevilla. Departamento de Química Orgánica |
Fecha de publicación | 2005 |
Fecha de depósito | 2018-02-19 |
Publicado en |
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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- ... 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. |
Agencias financiadoras | Ministerio de Ciencia y Tecnología (MCYT). España |
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. |
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A PRACTICAL SYNTHESIS.pdf | 177.5Kb | [PDF] | Ver/ | |