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

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 a...

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Autores: Ros Lao, Abel, Álvarez González, Eleuterio, Dietrich, Hansjörg, Batarda Fernandes, Rosario, Lassaletta Simón, José María
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2005
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/70420
Acceso en línea:https://hdl.handle.net/11441/70420
https://doi.org/10.1055/s-2005-921894
Access Level:acceso abierto
Palabra clave:Asymmetric synthesis
Cycloadditions
Heterocycles
Isoxazolines
Nitrile oxides
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spelling A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic AcidsRos Lao, AbelÁlvarez González, EleuterioDietrich, HansjörgBatarda Fernandes, RosarioLassaletta Simón, José MaríaAsymmetric synthesisCycloadditionsHeterocyclesIsoxazolinesNitrile oxidesThe 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.Ministerio de Ciencia y Tecnología CTQ2004-00290, CTQ2004-00241Química OrgánicaMinisterio de Ciencia y Tecnología (MCYT). España2005info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfapplication/pdfhttps://hdl.handle.net/11441/70420https://doi.org/10.1055/s-2005-921894reponame:idUS. Depósito de Investigación de la Universidad de Sevillainstname:Universidad de Sevilla (US)InglésSynlett, 19, 2899-2904.http://dx.doi.org/10.1055/s-2005-921894info:eu-repo/semantics/openAccessoai:idus.us.es:11441/704202026-06-17T12:51:07Z
dc.title.none.fl_str_mv A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids
title A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids
spellingShingle A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids
Ros Lao, Abel
Asymmetric synthesis
Cycloadditions
Heterocycles
Isoxazolines
Nitrile oxides
title_short A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids
title_full A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids
title_fullStr A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids
title_full_unstemmed A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids
title_sort A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids
dc.creator.none.fl_str_mv Ros Lao, Abel
Álvarez González, Eleuterio
Dietrich, Hansjörg
Batarda Fernandes, Rosario
Lassaletta Simón, José María
author Ros Lao, Abel
author_facet Ros Lao, Abel
Álvarez González, Eleuterio
Dietrich, Hansjörg
Batarda Fernandes, Rosario
Lassaletta Simón, José María
author_role author
author2 Álvarez González, Eleuterio
Dietrich, Hansjörg
Batarda Fernandes, Rosario
Lassaletta Simón, José María
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Química Orgánica
Ministerio de Ciencia y Tecnología (MCYT). España
dc.subject.none.fl_str_mv Asymmetric synthesis
Cycloadditions
Heterocycles
Isoxazolines
Nitrile oxides
topic Asymmetric synthesis
Cycloadditions
Heterocycles
Isoxazolines
Nitrile oxides
description 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.
publishDate 2005
dc.date.none.fl_str_mv 2005
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/11441/70420
https://doi.org/10.1055/s-2005-921894
url https://hdl.handle.net/11441/70420
https://doi.org/10.1055/s-2005-921894
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Synlett, 19, 2899-2904.
http://dx.doi.org/10.1055/s-2005-921894
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.source.none.fl_str_mv reponame:idUS. Depósito de Investigación de la Universidad de Sevilla
instname:Universidad de Sevilla (US)
instname_str Universidad de Sevilla (US)
reponame_str idUS. Depósito de Investigación de la Universidad de Sevilla
collection idUS. Depósito de Investigación de la Universidad de Sevilla
repository.name.fl_str_mv
repository.mail.fl_str_mv
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