Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts

Autores
Faraoni, María Belén; Ayala, Alicia D.; Vetere, Virginia; Casella, Mónica Laura; Ferretti, Osmar Alberto; Podesté, Julio C.
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A key step in the preparation of asymmetric heterogeneous catalysts based on silica-supported rhodium and platinum chemically modified with chiral organotins, is the synthesis of optically pure tin derivatives. We report on the synthetic pathways leading to the synthesis of (-)-menthyltin derivatives without the formation of epimerization by-products. The physical properties (including full 1H, 13C and 119Sn NMR spectra) of the new compounds, containing between one and three (-)-menthyl ligands attached to the tin atom, are reported. The preparation of two catalysts based on silica-supported rhodium and platinum chemically modified with (-)-menthyldiphenylmethyltin, as well as some studies on the catalytic hydrogenation of ethyl pyruvate, are also described. These studies show that the reductions lead to (R)- and (S)-ethyl lactates as the only products, that the (S) enantiomer was the isomer formed preferentially, and that the degree of conversion observed using both catalytic systems was almost quantitative (97-100%). The enantiomeric excesses observed were in the range 7-8%. One important advantage of these catalytic systems is their stability. Recycling of the used catalysts is possible, without any loss in the degree of conversion or enantiomeric excess.
Fil: Faraoni, María Belén. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Ayala, Alicia D.. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; 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 "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Ferretti, Osmar Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Podesté, Julio C.. Universidad Nacional del Sur. Departamento de Química; Argentina
Materia
Chiral Ligand
Heterogeneous Catalysts
Hydrogenation
Organotin
Synthesis
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:11336/55201
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/55201
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalystsFaraoni, María BelénAyala, Alicia D.Vetere, VirginiaCasella, Mónica LauraFerretti, Osmar AlbertoPodesté, Julio C.Chiral LigandHeterogeneous CatalystsHydrogenationOrganotinSynthesishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A key step in the preparation of asymmetric heterogeneous catalysts based on silica-supported rhodium and platinum chemically modified with chiral organotins, is the synthesis of optically pure tin derivatives. We report on the synthetic pathways leading to the synthesis of (-)-menthyltin derivatives without the formation of epimerization by-products. The physical properties (including full 1H, 13C and 119Sn NMR spectra) of the new compounds, containing between one and three (-)-menthyl ligands attached to the tin atom, are reported. The preparation of two catalysts based on silica-supported rhodium and platinum chemically modified with (-)-menthyldiphenylmethyltin, as well as some studies on the catalytic hydrogenation of ethyl pyruvate, are also described. These studies show that the reductions lead to (R)- and (S)-ethyl lactates as the only products, that the (S) enantiomer was the isomer formed preferentially, and that the degree of conversion observed using both catalytic systems was almost quantitative (97-100%). The enantiomeric excesses observed were in the range 7-8%. One important advantage of these catalytic systems is their stability. Recycling of the used catalysts is possible, without any loss in the degree of conversion or enantiomeric excess.Fil: Faraoni, María Belén. Universidad Nacional del Sur. Departamento de Química; ArgentinaFil: Ayala, Alicia D.. Universidad Nacional del Sur. Departamento de Química; ArgentinaFil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; 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 "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Ferretti, Osmar Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Podesté, Julio C.. Universidad Nacional del Sur. Departamento de Química; ArgentinaJohn Wiley & Sons Ltd2005-04info: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/11336/55201Faraoni, María Belén; Ayala, Alicia D.; Vetere, Virginia; Casella, Mónica Laura; Ferretti, Osmar Alberto; et al.; Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts; John Wiley & Sons Ltd; Applied Organometallic Chemistry; 19; 4; 4-2005; 465-4720268-2605CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/aoc.794info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/aoc.794info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-29T12:40:08Zoai:ri.conicet.gov.ar:11336/55201instacron: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:34982025-10-29 12:40:08.347CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts
title Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts
spellingShingle Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts
Faraoni, María Belén
Chiral Ligand
Heterogeneous Catalysts
Hydrogenation
Organotin
Synthesis
title_short Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts
title_full Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts
title_fullStr Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts
title_full_unstemmed Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts
title_sort Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts
dc.creator.none.fl_str_mv Faraoni, María Belén
Ayala, Alicia D.
Vetere, Virginia
Casella, Mónica Laura
Ferretti, Osmar Alberto
Podesté, Julio C.
author Faraoni, María Belén
author_facet Faraoni, María Belén
Ayala, Alicia D.
Vetere, Virginia
Casella, Mónica Laura
Ferretti, Osmar Alberto
Podesté, Julio C.
author_role author
author2 Ayala, Alicia D.
Vetere, Virginia
Casella, Mónica Laura
Ferretti, Osmar Alberto
Podesté, Julio C.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Chiral Ligand
Heterogeneous Catalysts
Hydrogenation
Organotin
Synthesis
topic Chiral Ligand
Heterogeneous Catalysts
Hydrogenation
Organotin
Synthesis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A key step in the preparation of asymmetric heterogeneous catalysts based on silica-supported rhodium and platinum chemically modified with chiral organotins, is the synthesis of optically pure tin derivatives. We report on the synthetic pathways leading to the synthesis of (-)-menthyltin derivatives without the formation of epimerization by-products. The physical properties (including full 1H, 13C and 119Sn NMR spectra) of the new compounds, containing between one and three (-)-menthyl ligands attached to the tin atom, are reported. The preparation of two catalysts based on silica-supported rhodium and platinum chemically modified with (-)-menthyldiphenylmethyltin, as well as some studies on the catalytic hydrogenation of ethyl pyruvate, are also described. These studies show that the reductions lead to (R)- and (S)-ethyl lactates as the only products, that the (S) enantiomer was the isomer formed preferentially, and that the degree of conversion observed using both catalytic systems was almost quantitative (97-100%). The enantiomeric excesses observed were in the range 7-8%. One important advantage of these catalytic systems is their stability. Recycling of the used catalysts is possible, without any loss in the degree of conversion or enantiomeric excess.
Fil: Faraoni, María Belén. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Ayala, Alicia D.. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; 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 "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Ferretti, Osmar Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Podesté, Julio C.. Universidad Nacional del Sur. Departamento de Química; Argentina
description A key step in the preparation of asymmetric heterogeneous catalysts based on silica-supported rhodium and platinum chemically modified with chiral organotins, is the synthesis of optically pure tin derivatives. We report on the synthetic pathways leading to the synthesis of (-)-menthyltin derivatives without the formation of epimerization by-products. The physical properties (including full 1H, 13C and 119Sn NMR spectra) of the new compounds, containing between one and three (-)-menthyl ligands attached to the tin atom, are reported. The preparation of two catalysts based on silica-supported rhodium and platinum chemically modified with (-)-menthyldiphenylmethyltin, as well as some studies on the catalytic hydrogenation of ethyl pyruvate, are also described. These studies show that the reductions lead to (R)- and (S)-ethyl lactates as the only products, that the (S) enantiomer was the isomer formed preferentially, and that the degree of conversion observed using both catalytic systems was almost quantitative (97-100%). The enantiomeric excesses observed were in the range 7-8%. One important advantage of these catalytic systems is their stability. Recycling of the used catalysts is possible, without any loss in the degree of conversion or enantiomeric excess.
publishDate 2005
dc.date.none.fl_str_mv 2005-04
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/11336/55201
Faraoni, María Belén; Ayala, Alicia D.; Vetere, Virginia; Casella, Mónica Laura; Ferretti, Osmar Alberto; et al.; Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts; John Wiley & Sons Ltd; Applied Organometallic Chemistry; 19; 4; 4-2005; 465-472
0268-2605
CONICET Digital
CONICET
url http://hdl.handle.net/11336/55201
identifier_str_mv Faraoni, María Belén; Ayala, Alicia D.; Vetere, Virginia; Casella, Mónica Laura; Ferretti, Osmar Alberto; et al.; Synthesis of chiral organotins suitable for the preparation of asymmetric heterogeneous catalysts; John Wiley & Sons Ltd; Applied Organometallic Chemistry; 19; 4; 4-2005; 465-472
0268-2605
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/aoc.794
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/aoc.794
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
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
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 13.10058

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