Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study

Autores
Vallejos, Margarita; Grimblat, Nicolas; Pellegrinet, Silvina Carla
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We have studied the Diels-Alder reactions of pinacol alkenylboronates with cyclopentadiene under two different sets of conditions: thermal heating at 170 C in a pressure tube and with catalytic TFA (5 mol%) at 80 °C. Yields varied significantly from system to system and also for the uncatalyzed and catalyzed methodologies. Moderate to excellent exo-stereoselectivities were obtained in all cases. The theoretical study of the thermal reactions sheds some light on the intriguing substituent effects observed experimentally. A variety of substituted 5-norbornen-2-ols were easily generated by subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide.
Fil: Vallejos, Margarita. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Grimblat, Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
Diels-Alder
Alkenylboronates
Dft
Reversibility
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/29060
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical studyVallejos, MargaritaGrimblat, NicolasPellegrinet, Silvina CarlaDiels-AlderAlkenylboronatesDftReversibilityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We have studied the Diels-Alder reactions of pinacol alkenylboronates with cyclopentadiene under two different sets of conditions: thermal heating at 170 C in a pressure tube and with catalytic TFA (5 mol%) at 80 °C. Yields varied significantly from system to system and also for the uncatalyzed and catalyzed methodologies. Moderate to excellent exo-stereoselectivities were obtained in all cases. The theoretical study of the thermal reactions sheds some light on the intriguing substituent effects observed experimentally. A variety of substituted 5-norbornen-2-ols were easily generated by subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide.Fil: Vallejos, Margarita. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Grimblat, Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaRoyal Society of Chemistry2014-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/29060Vallejos, Margarita; Grimblat, Nicolas; Pellegrinet, Silvina Carla; Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study; Royal Society of Chemistry; RSC Advances; 4; 68; 8-2014; 36385-364002046-20692046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/C4RA07415G#!divAbstractinfo:eu-repo/semantics/altIdentifier/doi/10.1039/c4ra07415ginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:45:56Zoai:ri.conicet.gov.ar:11336/29060instacron: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:34982025-10-15 15:45:56.97CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
title Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
spellingShingle Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
Vallejos, Margarita
Diels-Alder
Alkenylboronates
Dft
Reversibility
title_short Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
title_full Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
title_fullStr Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
title_full_unstemmed Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
title_sort Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study
dc.creator.none.fl_str_mv Vallejos, Margarita
Grimblat, Nicolas
Pellegrinet, Silvina Carla
author Vallejos, Margarita
author_facet Vallejos, Margarita
Grimblat, Nicolas
Pellegrinet, Silvina Carla
author_role author
author2 Grimblat, Nicolas
Pellegrinet, Silvina Carla
author2_role author
author
dc.subject.none.fl_str_mv Diels-Alder
Alkenylboronates
Dft
Reversibility
topic Diels-Alder
Alkenylboronates
Dft
Reversibility
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv We have studied the Diels-Alder reactions of pinacol alkenylboronates with cyclopentadiene under two different sets of conditions: thermal heating at 170 C in a pressure tube and with catalytic TFA (5 mol%) at 80 °C. Yields varied significantly from system to system and also for the uncatalyzed and catalyzed methodologies. Moderate to excellent exo-stereoselectivities were obtained in all cases. The theoretical study of the thermal reactions sheds some light on the intriguing substituent effects observed experimentally. A variety of substituted 5-norbornen-2-ols were easily generated by subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide.
Fil: Vallejos, Margarita. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Grimblat, Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description We have studied the Diels-Alder reactions of pinacol alkenylboronates with cyclopentadiene under two different sets of conditions: thermal heating at 170 C in a pressure tube and with catalytic TFA (5 mol%) at 80 °C. Yields varied significantly from system to system and also for the uncatalyzed and catalyzed methodologies. Moderate to excellent exo-stereoselectivities were obtained in all cases. The theoretical study of the thermal reactions sheds some light on the intriguing substituent effects observed experimentally. A variety of substituted 5-norbornen-2-ols were easily generated by subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide.
publishDate 2014
dc.date.none.fl_str_mv 2014-08
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/11336/29060
Vallejos, Margarita; Grimblat, Nicolas; Pellegrinet, Silvina Carla; Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study; Royal Society of Chemistry; RSC Advances; 4; 68; 8-2014; 36385-36400
2046-2069
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/29060
identifier_str_mv Vallejos, Margarita; Grimblat, Nicolas; Pellegrinet, Silvina Carla; Diels-Alder Reactions of Pinacol Alkenylboronates: An experimental and theoretical study; Royal Society of Chemistry; RSC Advances; 4; 68; 8-2014; 36385-36400
2046-2069
CONICET Digital
CONICET
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/2014/RA/C4RA07415G#!divAbstract
info:eu-repo/semantics/altIdentifier/doi/10.1039/c4ra07415g
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
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 13.22299

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