Theoretical investigation of the Diels-Alder reactions of unsaturated boronates

Autores
Pellegrinet, Silvina Carla; Grimblat, Nicolas
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The Diels-Alder reactions of simple unsaturated boronates have been investigated using computational methods and the results were compared with those for the analogue dihalo- and dialkylboranes. Our results indicate that the activating effect of the boronate moiety is small. All the studied reactions are concerted normal electron-demand Diels-Alder reactions with asynchronous transition structures and weak [4 + 3] C-B secondary orbital interactions, which explains the low experimental reactivity. Both electronic and steric effects contribute to give the observed low stereo- and regioselectivities.
Fil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Grimblat, Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Materia
Theoretical Investigation
Diels-Alder Reaction
Boronates
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/6052
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/6052
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Theoretical investigation of the Diels-Alder reactions of unsaturated boronatesPellegrinet, Silvina CarlaGrimblat, NicolasTheoretical InvestigationDiels-Alder ReactionBoronateshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The Diels-Alder reactions of simple unsaturated boronates have been investigated using computational methods and the results were compared with those for the analogue dihalo- and dialkylboranes. Our results indicate that the activating effect of the boronate moiety is small. All the studied reactions are concerted normal electron-demand Diels-Alder reactions with asynchronous transition structures and weak [4 + 3] C-B secondary orbital interactions, which explains the low experimental reactivity. Both electronic and steric effects contribute to give the observed low stereo- and regioselectivities.Fil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Grimblat, Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaRoyal Society of Chemistry2013-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6052Pellegrinet, Silvina Carla; Grimblat, Nicolas; Theoretical investigation of the Diels-Alder reactions of unsaturated boronates; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 11; 22; 4-2013; 3733-37411477-0520enginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/c3ob40146dinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C3OB40146Dinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:06:06Zoai:ri.conicet.gov.ar:11336/6052instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:06:07.071CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Theoretical investigation of the Diels-Alder reactions of unsaturated boronates
title Theoretical investigation of the Diels-Alder reactions of unsaturated boronates
spellingShingle Theoretical investigation of the Diels-Alder reactions of unsaturated boronates
Pellegrinet, Silvina Carla
Theoretical Investigation
Diels-Alder Reaction
Boronates
title_short Theoretical investigation of the Diels-Alder reactions of unsaturated boronates
title_full Theoretical investigation of the Diels-Alder reactions of unsaturated boronates
title_fullStr Theoretical investigation of the Diels-Alder reactions of unsaturated boronates
title_full_unstemmed Theoretical investigation of the Diels-Alder reactions of unsaturated boronates
title_sort Theoretical investigation of the Diels-Alder reactions of unsaturated boronates
dc.creator.none.fl_str_mv Pellegrinet, Silvina Carla
Grimblat, Nicolas
author Pellegrinet, Silvina Carla
author_facet Pellegrinet, Silvina Carla
Grimblat, Nicolas
author_role author
author2 Grimblat, Nicolas
author2_role author
dc.subject.none.fl_str_mv Theoretical Investigation
Diels-Alder Reaction
Boronates
topic Theoretical Investigation
Diels-Alder Reaction
Boronates
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The Diels-Alder reactions of simple unsaturated boronates have been investigated using computational methods and the results were compared with those for the analogue dihalo- and dialkylboranes. Our results indicate that the activating effect of the boronate moiety is small. All the studied reactions are concerted normal electron-demand Diels-Alder reactions with asynchronous transition structures and weak [4 + 3] C-B secondary orbital interactions, which explains the low experimental reactivity. Both electronic and steric effects contribute to give the observed low stereo- and regioselectivities.
Fil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Grimblat, Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
description The Diels-Alder reactions of simple unsaturated boronates have been investigated using computational methods and the results were compared with those for the analogue dihalo- and dialkylboranes. Our results indicate that the activating effect of the boronate moiety is small. All the studied reactions are concerted normal electron-demand Diels-Alder reactions with asynchronous transition structures and weak [4 + 3] C-B secondary orbital interactions, which explains the low experimental reactivity. Both electronic and steric effects contribute to give the observed low stereo- and regioselectivities.
publishDate 2013
dc.date.none.fl_str_mv 2013-04
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/6052
Pellegrinet, Silvina Carla; Grimblat, Nicolas; Theoretical investigation of the Diels-Alder reactions of unsaturated boronates; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 11; 22; 4-2013; 3733-3741
1477-0520
url http://hdl.handle.net/11336/6052
identifier_str_mv Pellegrinet, Silvina Carla; Grimblat, Nicolas; Theoretical investigation of the Diels-Alder reactions of unsaturated boronates; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 11; 22; 4-2013; 3733-3741
1477-0520
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/c3ob40146d
info:eu-repo/semantics/altIdentifier/doi/10.1039/C3OB40146D
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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