Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto Nitrile

[EN]Radical cascade cyclizations of unsaturated epoxy­nitriles induced by titanocene chloride proceed in good yields and with excellent diastereoselectivities. From three to seven stereocenters were created by the reaction and a single isomeric product was obtained from most of the substrates examin...

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Detalles Bibliográficos
Autores: Fernández Mateos, Alfonso, Herrero Teijón, Pablo, Rabanedo Clemente, R., Rubio González, María Rosa, Sanz González, Francisca
Tipo de recurso: artículo
Estado:Versión enviada para evaluación y publicación
Fecha de publicación:2007
País:España
Institución:Universidad de Salamanca (USAL)
Repositorio:GREDOS. Repositorio Institucional de la Universidad de Salamanca
OAI Identifier:oai:gredos.usal.es:10366/154289
Acceso en línea:http://hdl.handle.net/10366/154289
Access Level:acceso embargado
Palabra clave:Radical cyclization
Titanocene chloride
Epoxynitriles
Cascade reactions
2306 Química Orgánica
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spelling Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto NitrileFernández Mateos, AlfonsoHerrero Teijón, PabloRabanedo Clemente, R.Rubio González, María RosaSanz González, FranciscaRadical cyclizationTitanocene chlorideEpoxynitrilesCascade reactions2306 Química Orgánica[EN]Radical cascade cyclizations of unsaturated epoxy­nitriles induced by titanocene chloride proceed in good yields and with excellent diastereoselectivities. From three to seven stereocenters were created by the reaction and a single isomeric product was obtained from most of the substrates examined. The relative configuration of the products is consistent with cyclization occurring via a chair-like transition state. The termination of the radical cascade reaction by 4-exo, 5-exo or 6-exo cyclization onto nitrile is remarkable.info202420242007info:eu-repo/semantics/articleinfo:eu-repo/semantics/submittedVersionapplication/pdfhttp://hdl.handle.net/10366/154289reponame:GREDOS. Repositorio Institucional de la Universidad de Salamancainstname:Universidad de Salamanca (USAL)InglésAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/embargoedAccessoai:gredos.usal.es:10366/1542892026-06-07T06:28:51Z
dc.title.none.fl_str_mv Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto Nitrile
title Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto Nitrile
spellingShingle Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto Nitrile
Fernández Mateos, Alfonso
Radical cyclization
Titanocene chloride
Epoxynitriles
Cascade reactions
2306 Química Orgánica
title_short Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto Nitrile
title_full Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto Nitrile
title_fullStr Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto Nitrile
title_full_unstemmed Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto Nitrile
title_sort Stereoselective Radical Cascade Cyclizations of Unsaturated Epoxynitriles: Quadruple Radical Cyclization Terminated by a 4-exo Process onto Nitrile
dc.creator.none.fl_str_mv Fernández Mateos, Alfonso
Herrero Teijón, Pablo
Rabanedo Clemente, R.
Rubio González, María Rosa
Sanz González, Francisca
author Fernández Mateos, Alfonso
author_facet Fernández Mateos, Alfonso
Herrero Teijón, Pablo
Rabanedo Clemente, R.
Rubio González, María Rosa
Sanz González, Francisca
author_role author
author2 Herrero Teijón, Pablo
Rabanedo Clemente, R.
Rubio González, María Rosa
Sanz González, Francisca
author2_role author
author
author
author
dc.subject.none.fl_str_mv Radical cyclization
Titanocene chloride
Epoxynitriles
Cascade reactions
2306 Química Orgánica
topic Radical cyclization
Titanocene chloride
Epoxynitriles
Cascade reactions
2306 Química Orgánica
description [EN]Radical cascade cyclizations of unsaturated epoxy­nitriles induced by titanocene chloride proceed in good yields and with excellent diastereoselectivities. From three to seven stereocenters were created by the reaction and a single isomeric product was obtained from most of the substrates examined. The relative configuration of the products is consistent with cyclization occurring via a chair-like transition state. The termination of the radical cascade reaction by 4-exo, 5-exo or 6-exo cyclization onto nitrile is remarkable.
publishDate 2007
dc.date.none.fl_str_mv 2007
2024
2024
info
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/submittedVersion
format article
status_str submittedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10366/154289
url http://hdl.handle.net/10366/154289
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/embargoedAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv embargoedAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:GREDOS. Repositorio Institucional de la Universidad de Salamanca
instname:Universidad de Salamanca (USAL)
instname_str Universidad de Salamanca (USAL)
reponame_str GREDOS. Repositorio Institucional de la Universidad de Salamanca
collection GREDOS. Repositorio Institucional de la Universidad de Salamanca
repository.name.fl_str_mv
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score 15.300724

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