Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers

Autores
Ruggera, José Fernando; Merlo, Andrea Beatriz; Pis Diez, Reinaldo; Casella, Mónica Laura
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The enantioselective hydrogenation of ethyl pyruvate using a Pt/SiO2 catalyst modified with six different chiral modifiers was studied. The chiral modifiers chosen were: (S)-(+)-1-aminoindan, (R)-(−)-1-aminoindan, (1R,2S)-(+)-cis-1- amino-2-indanol, (1S,2R)-(−)-cis-1-amino-2-indanol, (S)-(+)-1-indanol and (R)-(−)-1-indanol.An excess of the (R) enantiomer of the product of 63% and 45% with (S)-(+)-1-aminoindan and (R)-(−)-1-aminoindan modifiers, respectively was obtained. When using (1S,2R)-(−)-cis-1-amino-2-indanol and (1R,2S)-(+)-cis-1-amino-2-indanol, the enantiomeric excess (ee%) obtained was 30% and 5%, respectively, while with both indanols ee% did not exceed 8%. Molecular modeling of the complex formed between the chiral modifier and ethyl pyruvate performed by DFT calculations allowed predicting the values of ee% obtained experimentally. The low ee% value obtained both aminoindanol chiral modifiers were used, could be explained by the analysis of non-covalent interactions (NCI) method. These calculations demonstrated the presence of an intramolecular hydrogen bond in the structure of these modifiers.
Fil: Ruggera, José Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Merlo, Andrea Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Pis Diez, Reinaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica ; 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
ETHYL PYRUVATE
NON-CINCHONA MODIFIERS
DFT
PLATINUM
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:11336/41639
Acceder
id CONICETDig_2c01cb2ade3882784981395cf9f817ba
oai_identifier_str oai:ri.conicet.gov.ar:11336/41639
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiersRuggera, José FernandoMerlo, Andrea BeatrizPis Diez, ReinaldoCasella, Mónica LauraENANTIOSELECTIVITYETHYL PYRUVATENON-CINCHONA MODIFIERSDFTPLATINUMhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The enantioselective hydrogenation of ethyl pyruvate using a Pt/SiO2 catalyst modified with six different chiral modifiers was studied. The chiral modifiers chosen were: (S)-(+)-1-aminoindan, (R)-(−)-1-aminoindan, (1R,2S)-(+)-cis-1- amino-2-indanol, (1S,2R)-(−)-cis-1-amino-2-indanol, (S)-(+)-1-indanol and (R)-(−)-1-indanol.An excess of the (R) enantiomer of the product of 63% and 45% with (S)-(+)-1-aminoindan and (R)-(−)-1-aminoindan modifiers, respectively was obtained. When using (1S,2R)-(−)-cis-1-amino-2-indanol and (1R,2S)-(+)-cis-1-amino-2-indanol, the enantiomeric excess (ee%) obtained was 30% and 5%, respectively, while with both indanols ee% did not exceed 8%. Molecular modeling of the complex formed between the chiral modifier and ethyl pyruvate performed by DFT calculations allowed predicting the values of ee% obtained experimentally. The low ee% value obtained both aminoindanol chiral modifiers were used, could be explained by the analysis of non-covalent interactions (NCI) method. These calculations demonstrated the presence of an intramolecular hydrogen bond in the structure of these modifiers.Fil: Ruggera, José Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; ArgentinaFil: Merlo, Andrea Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; ArgentinaFil: Pis Diez, Reinaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica ; 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 Science2016-11info: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/11336/41639Ruggera, José Fernando; Merlo, Andrea Beatriz; Pis Diez, Reinaldo; Casella, Mónica Laura; Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers; Elsevier Science; Journal of Molecular Catalysis A: Chemical; 423; 11-2016; 233-2391381-1169CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcata.2016.07.009info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S138111691630259Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:11:26Zoai:ri.conicet.gov.ar:11336/41639instacron: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:34982025-10-22 12:11:26.953CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
spellingShingle Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
Ruggera, José Fernando
ENANTIOSELECTIVITY
ETHYL PYRUVATE
NON-CINCHONA MODIFIERS
DFT
PLATINUM
title_short Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title_full Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title_fullStr Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title_full_unstemmed Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
title_sort Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
dc.creator.none.fl_str_mv Ruggera, José Fernando
Merlo, Andrea Beatriz
Pis Diez, Reinaldo
Casella, Mónica Laura
author Ruggera, José Fernando
author_facet Ruggera, José Fernando
Merlo, Andrea Beatriz
Pis Diez, Reinaldo
Casella, Mónica Laura
author_role author
author2 Merlo, Andrea Beatriz
Pis Diez, Reinaldo
Casella, Mónica Laura
author2_role author
author
author
dc.subject.none.fl_str_mv ENANTIOSELECTIVITY
ETHYL PYRUVATE
NON-CINCHONA MODIFIERS
DFT
PLATINUM
topic ENANTIOSELECTIVITY
ETHYL PYRUVATE
NON-CINCHONA MODIFIERS
DFT
PLATINUM
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 enantioselective hydrogenation of ethyl pyruvate using a Pt/SiO2 catalyst modified with six different chiral modifiers was studied. The chiral modifiers chosen were: (S)-(+)-1-aminoindan, (R)-(−)-1-aminoindan, (1R,2S)-(+)-cis-1- amino-2-indanol, (1S,2R)-(−)-cis-1-amino-2-indanol, (S)-(+)-1-indanol and (R)-(−)-1-indanol.An excess of the (R) enantiomer of the product of 63% and 45% with (S)-(+)-1-aminoindan and (R)-(−)-1-aminoindan modifiers, respectively was obtained. When using (1S,2R)-(−)-cis-1-amino-2-indanol and (1R,2S)-(+)-cis-1-amino-2-indanol, the enantiomeric excess (ee%) obtained was 30% and 5%, respectively, while with both indanols ee% did not exceed 8%. Molecular modeling of the complex formed between the chiral modifier and ethyl pyruvate performed by DFT calculations allowed predicting the values of ee% obtained experimentally. The low ee% value obtained both aminoindanol chiral modifiers were used, could be explained by the analysis of non-covalent interactions (NCI) method. These calculations demonstrated the presence of an intramolecular hydrogen bond in the structure of these modifiers.
Fil: Ruggera, José Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Merlo, Andrea Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Pis Diez, Reinaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica ; 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 The enantioselective hydrogenation of ethyl pyruvate using a Pt/SiO2 catalyst modified with six different chiral modifiers was studied. The chiral modifiers chosen were: (S)-(+)-1-aminoindan, (R)-(−)-1-aminoindan, (1R,2S)-(+)-cis-1- amino-2-indanol, (1S,2R)-(−)-cis-1-amino-2-indanol, (S)-(+)-1-indanol and (R)-(−)-1-indanol.An excess of the (R) enantiomer of the product of 63% and 45% with (S)-(+)-1-aminoindan and (R)-(−)-1-aminoindan modifiers, respectively was obtained. When using (1S,2R)-(−)-cis-1-amino-2-indanol and (1R,2S)-(+)-cis-1-amino-2-indanol, the enantiomeric excess (ee%) obtained was 30% and 5%, respectively, while with both indanols ee% did not exceed 8%. Molecular modeling of the complex formed between the chiral modifier and ethyl pyruvate performed by DFT calculations allowed predicting the values of ee% obtained experimentally. The low ee% value obtained both aminoindanol chiral modifiers were used, could be explained by the analysis of non-covalent interactions (NCI) method. These calculations demonstrated the presence of an intramolecular hydrogen bond in the structure of these modifiers.
publishDate 2016
dc.date.none.fl_str_mv 2016-11
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/11336/41639
Ruggera, José Fernando; Merlo, Andrea Beatriz; Pis Diez, Reinaldo; Casella, Mónica Laura; Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers; Elsevier Science; Journal of Molecular Catalysis A: Chemical; 423; 11-2016; 233-239
1381-1169
CONICET Digital
CONICET
url http://hdl.handle.net/11336/41639
identifier_str_mv Ruggera, José Fernando; Merlo, Andrea Beatriz; Pis Diez, Reinaldo; Casella, Mónica Laura; Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers; Elsevier Science; Journal of Molecular Catalysis A: Chemical; 423; 11-2016; 233-239
1381-1169
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcata.2016.07.009
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S138111691630259X
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
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
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score 12.982451

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