Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione

Autores
Vetere, Virginia; Faraoni, María Belén; Podestá, Julio Cesar; Casella, Mónica Laura
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this paper we have studied the liquid-phase enantioselective hydrogenation of 3,4-hexanedione using Pt-based catalysts, modified with chiral organotin compounds derived from the (−)-menthyl group: (−)-Pt-MenSnBu3 and (−)-Men3Sn-Sn-(−)-Men3. The organotin chiral modifiers were carefully synthesizedand characterized in order to obtain optically pure compounds. The catalysts were prepared through a controlled surface reaction between the supported transitionmetal and the organometallic compound, using techniques derived from Surface Organometallic Chemistry on Metals (SOMC/M). The organobimetallic catalytic systems were found to be active and enantioselective in the hydrogenation of 3,4-hexanedione, yielding an enantiomeric excess of 25–27% for 4-hydroxy-3-hexanone.
Fil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Casella, Mónica Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Materia
Enantioselectivity
3,4-Hexanedione
Hydrogenation
(-)-Menthyl Derivatives
Ptsn
Somc/M
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/41322
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedioneVetere, VirginiaFaraoni, María BelénPodestá, Julio CesarCasella, Mónica LauraEnantioselectivity3,4-HexanedioneHydrogenation(-)-Menthyl DerivativesPtsnSomc/Mhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this paper we have studied the liquid-phase enantioselective hydrogenation of 3,4-hexanedione using Pt-based catalysts, modified with chiral organotin compounds derived from the (−)-menthyl group: (−)-Pt-MenSnBu3 and (−)-Men3Sn-Sn-(−)-Men3. The organotin chiral modifiers were carefully synthesizedand characterized in order to obtain optically pure compounds. The catalysts were prepared through a controlled surface reaction between the supported transitionmetal and the organometallic compound, using techniques derived from Surface Organometallic Chemistry on Metals (SOMC/M). The organobimetallic catalytic systems were found to be active and enantioselective in the hydrogenation of 3,4-hexanedione, yielding an enantiomeric excess of 25–27% for 4-hydroxy-3-hexanone.Fil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; ArgentinaFil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Casella, Mónica Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; ArgentinaElsevier Science2012-11-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/41322Vetere, Virginia; Faraoni, María Belén; Podestá, Julio Cesar; Casella, Mónica Laura; Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione; Elsevier Science; Applied Catalysis A: General; 445-446; 1-11-2012; 209-2140926-860XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/journal/0926860X/445-446info:eu-repo/semantics/altIdentifier/doi/10.1016/j.apcata.2012.08.031info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:33:28Zoai:ri.conicet.gov.ar:11336/41322instacron: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:34982025-11-12 09:33:29.006CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
title Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
spellingShingle Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
Vetere, Virginia
Enantioselectivity
3,4-Hexanedione
Hydrogenation
(-)-Menthyl Derivatives
Ptsn
Somc/M
title_short Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
title_full Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
title_fullStr Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
title_full_unstemmed Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
title_sort Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
dc.creator.none.fl_str_mv Vetere, Virginia
Faraoni, María Belén
Podestá, Julio Cesar
Casella, Mónica Laura
author Vetere, Virginia
author_facet Vetere, Virginia
Faraoni, María Belén
Podestá, Julio Cesar
Casella, Mónica Laura
author_role author
author2 Faraoni, María Belén
Podestá, Julio Cesar
Casella, Mónica Laura
author2_role author
author
author
dc.subject.none.fl_str_mv Enantioselectivity
3,4-Hexanedione
Hydrogenation
(-)-Menthyl Derivatives
Ptsn
Somc/M
topic Enantioselectivity
3,4-Hexanedione
Hydrogenation
(-)-Menthyl Derivatives
Ptsn
Somc/M
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this paper we have studied the liquid-phase enantioselective hydrogenation of 3,4-hexanedione using Pt-based catalysts, modified with chiral organotin compounds derived from the (−)-menthyl group: (−)-Pt-MenSnBu3 and (−)-Men3Sn-Sn-(−)-Men3. The organotin chiral modifiers were carefully synthesizedand characterized in order to obtain optically pure compounds. The catalysts were prepared through a controlled surface reaction between the supported transitionmetal and the organometallic compound, using techniques derived from Surface Organometallic Chemistry on Metals (SOMC/M). The organobimetallic catalytic systems were found to be active and enantioselective in the hydrogenation of 3,4-hexanedione, yielding an enantiomeric excess of 25–27% for 4-hydroxy-3-hexanone.
Fil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Casella, Mónica Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
description In this paper we have studied the liquid-phase enantioselective hydrogenation of 3,4-hexanedione using Pt-based catalysts, modified with chiral organotin compounds derived from the (−)-menthyl group: (−)-Pt-MenSnBu3 and (−)-Men3Sn-Sn-(−)-Men3. The organotin chiral modifiers were carefully synthesizedand characterized in order to obtain optically pure compounds. The catalysts were prepared through a controlled surface reaction between the supported transitionmetal and the organometallic compound, using techniques derived from Surface Organometallic Chemistry on Metals (SOMC/M). The organobimetallic catalytic systems were found to be active and enantioselective in the hydrogenation of 3,4-hexanedione, yielding an enantiomeric excess of 25–27% for 4-hydroxy-3-hexanone.
publishDate 2012
dc.date.none.fl_str_mv 2012-11-01
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/11336/41322
Vetere, Virginia; Faraoni, María Belén; Podestá, Julio Cesar; Casella, Mónica Laura; Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione; Elsevier Science; Applied Catalysis A: General; 445-446; 1-11-2012; 209-214
0926-860X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/41322
identifier_str_mv Vetere, Virginia; Faraoni, María Belén; Podestá, Julio Cesar; Casella, Mónica Laura; Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione; Elsevier Science; Applied Catalysis A: General; 445-446; 1-11-2012; 209-214
0926-860X
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://www.sciencedirect.com/science/journal/0926860X/445-446
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.apcata.2012.08.031
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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
_version_ 1848597057377402880
score 13.137801

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