Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride

Autores
Faraoni, María Belén; Gerbino, Darío César; Podestá, Julio Cesar
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This paper reports results obtained in a study on the palladium-catalyzed hydrostannation of substituted propargyl alcohols with the bulky trineophyltin hydride (1). The reaction of 1 with 10 propargyl alcohols containing one up to three substituents, was carried out in THF at room temperature leading to the corresponding allylstannanes following in all cases a syn addition stereochemistry. These additions took place in good to excellent yields and, mostly, with a high degree of stereoselectivity. The results obtained suggest that the observed α/β regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full 1H-, 13C-, and 119Sn NMR characteristics are included. © 2008 Elsevier B.V. All rights reserved.
Fil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Materia
Hydrostannation
Palladium Catalyzed
Propargyl Alcohols
Stannylated Allyl Alcohols
Stereoselectivity
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:11336/66020
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/66020
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydrideFaraoni, María BelénGerbino, Darío CésarPodestá, Julio CesarHydrostannationPalladium CatalyzedPropargyl AlcoholsStannylated Allyl AlcoholsStereoselectivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This paper reports results obtained in a study on the palladium-catalyzed hydrostannation of substituted propargyl alcohols with the bulky trineophyltin hydride (1). The reaction of 1 with 10 propargyl alcohols containing one up to three substituents, was carried out in THF at room temperature leading to the corresponding allylstannanes following in all cases a syn addition stereochemistry. These additions took place in good to excellent yields and, mostly, with a high degree of stereoselectivity. The results obtained suggest that the observed α/β regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full 1H-, 13C-, and 119Sn NMR characteristics are included. © 2008 Elsevier B.V. All rights reserved.Fil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; ArgentinaFil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; ArgentinaFil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; ArgentinaElsevier Science Sa2008-05info: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/11336/66020Faraoni, María Belén; Gerbino, Darío César; Podestá, Julio Cesar; Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride; Elsevier Science Sa; Journal of Organometallic Chemistry; 693; 10; 5-2008; 1877-18850022-328XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022328X08001125info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jorganchem.2008.02.015info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:55:08Zoai:ri.conicet.gov.ar:11336/66020instacron: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 09:55:09.163CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
title Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
spellingShingle Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
Faraoni, María Belén
Hydrostannation
Palladium Catalyzed
Propargyl Alcohols
Stannylated Allyl Alcohols
Stereoselectivity
title_short Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
title_full Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
title_fullStr Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
title_full_unstemmed Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
title_sort Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
dc.creator.none.fl_str_mv Faraoni, María Belén
Gerbino, Darío César
Podestá, Julio Cesar
author Faraoni, María Belén
author_facet Faraoni, María Belén
Gerbino, Darío César
Podestá, Julio Cesar
author_role author
author2 Gerbino, Darío César
Podestá, Julio Cesar
author2_role author
author
dc.subject.none.fl_str_mv Hydrostannation
Palladium Catalyzed
Propargyl Alcohols
Stannylated Allyl Alcohols
Stereoselectivity
topic Hydrostannation
Palladium Catalyzed
Propargyl Alcohols
Stannylated Allyl Alcohols
Stereoselectivity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv This paper reports results obtained in a study on the palladium-catalyzed hydrostannation of substituted propargyl alcohols with the bulky trineophyltin hydride (1). The reaction of 1 with 10 propargyl alcohols containing one up to three substituents, was carried out in THF at room temperature leading to the corresponding allylstannanes following in all cases a syn addition stereochemistry. These additions took place in good to excellent yields and, mostly, with a high degree of stereoselectivity. The results obtained suggest that the observed α/β regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full 1H-, 13C-, and 119Sn NMR characteristics are included. © 2008 Elsevier B.V. All rights reserved.
Fil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
description This paper reports results obtained in a study on the palladium-catalyzed hydrostannation of substituted propargyl alcohols with the bulky trineophyltin hydride (1). The reaction of 1 with 10 propargyl alcohols containing one up to three substituents, was carried out in THF at room temperature leading to the corresponding allylstannanes following in all cases a syn addition stereochemistry. These additions took place in good to excellent yields and, mostly, with a high degree of stereoselectivity. The results obtained suggest that the observed α/β regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full 1H-, 13C-, and 119Sn NMR characteristics are included. © 2008 Elsevier B.V. All rights reserved.
publishDate 2008
dc.date.none.fl_str_mv 2008-05
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/11336/66020
Faraoni, María Belén; Gerbino, Darío César; Podestá, Julio Cesar; Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride; Elsevier Science Sa; Journal of Organometallic Chemistry; 693; 10; 5-2008; 1877-1885
0022-328X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/66020
identifier_str_mv Faraoni, María Belén; Gerbino, Darío César; Podestá, Julio Cesar; Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride; Elsevier Science Sa; Journal of Organometallic Chemistry; 693; 10; 5-2008; 1877-1885
0022-328X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022328X08001125
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jorganchem.2008.02.015
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 Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
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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