dc.creator | Ros Lao, Abel | es |
dc.creator | Álvarez González, Eleuterio | es |
dc.creator | Dietrich, Hansjörg | es |
dc.creator | Batarda Fernandes, Rosario | es |
dc.creator | Lassaletta Simón, José María | es |
dc.date.accessioned | 2018-02-19T15:46:54Z | |
dc.date.available | 2018-02-19T15:46:54Z | |
dc.date.issued | 2005 | |
dc.identifier.citation | 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. | |
dc.identifier.issn | 0936-5214 | es |
dc.identifier.uri | https://hdl.handle.net/11441/70420 | |
dc.description.abstract | 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. | es |
dc.description.sponsorship | Ministerio de Ciencia y Tecnología CTQ2004-00290, CTQ2004-00241 | es |
dc.format | application/pdf | es |
dc.language.iso | eng | es |
dc.relation.ispartof | Synlett, 19, 2899-2904. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.subject | Asymmetric synthesis | es |
dc.subject | Cycloadditions | es |
dc.subject | Heterocycles | es |
dc.subject | Isoxazolines | es |
dc.subject | Nitrile oxides | es |
dc.title | A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids | es |
dc.type | info:eu-repo/semantics/article | es |
dcterms.identifier | https://ror.org/03yxnpp24 | |
dc.type.version | info:eu-repo/semantics/publishedVersion | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química Orgánica | es |
dc.relation.publisherversion | http://dx.doi.org/10.1055/s-2005-921894 | es |
dc.identifier.doi | 10.1055/s-2005-921894 | es |
idus.format.extent | 6 | es |
dc.journaltitle | Synlett | es |
dc.publication.issue | 19 | es |
dc.publication.initialPage | 2899 | es |
dc.publication.endPage | 2904 | es |
dc.contributor.funder | Ministerio de Ciencia y Tecnología (MCYT). España | |