Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures

Autores
Bisogno, Fabricio Román; Fernández, María del Rosario; Lassaletta, José María; de Gonzalo, Gonzalo
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Room temperature ionic liquids (RTILs) have been widely used as (co)solvents in several catalytic processes modifying, in most of the cases, the catalyst activity and/or the selectivity for the studied reactions. However, there are just a few examples of their use in hydrogen bonding organocatalysis. In this paper, we show the positive effect of a set of imidazole-based ionic liquids ([bmim]BF4 and [hmim]PF6 ) in the enantioselective addition of formaldehyde tert-butylhydrazone to prochiral α-keto esters catalyzed by a sugar-based chiral thiourea. Reactions performed in the presence of low percentages of RTILs led to an increase of the catalyst activity, thereby making possible to work at lower temperatures. Thus, the chiral tert-butyl azomethyl tertiary alcohols could be obtained with moderate to good conversions and higher enantioselectivities for most of the studied substrates when using up to 30 vol% of [hmim]PF6 as a cosolvent in processes performed in toluene.
Fil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Fernández, María del Rosario. Universidad de Sevilla; España
Fil: Lassaletta, José María. Instituto de Investigaciones Químicas; España. Centro de Innovación en Química Avanzada; España
Fil: de Gonzalo, Gonzalo. Universidad de Sevilla; España
Materia
ASYMMETRIC CATALYSIS
ENE-TYPE REACTIONS
IONIC LIQUIDS
ORGANOCATALYSIS
SOLVENT ENGINEERING
TERTIARY ALCOHOLS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/172965
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperaturesBisogno, Fabricio RománFernández, María del RosarioLassaletta, José Maríade Gonzalo, GonzaloASYMMETRIC CATALYSISENE-TYPE REACTIONSIONIC LIQUIDSORGANOCATALYSISSOLVENT ENGINEERINGTERTIARY ALCOHOLShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2Room temperature ionic liquids (RTILs) have been widely used as (co)solvents in several catalytic processes modifying, in most of the cases, the catalyst activity and/or the selectivity for the studied reactions. However, there are just a few examples of their use in hydrogen bonding organocatalysis. In this paper, we show the positive effect of a set of imidazole-based ionic liquids ([bmim]BF4 and [hmim]PF6 ) in the enantioselective addition of formaldehyde tert-butylhydrazone to prochiral α-keto esters catalyzed by a sugar-based chiral thiourea. Reactions performed in the presence of low percentages of RTILs led to an increase of the catalyst activity, thereby making possible to work at lower temperatures. Thus, the chiral tert-butyl azomethyl tertiary alcohols could be obtained with moderate to good conversions and higher enantioselectivities for most of the studied substrates when using up to 30 vol% of [hmim]PF6 as a cosolvent in processes performed in toluene.Fil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Fernández, María del Rosario. Universidad de Sevilla; EspañaFil: Lassaletta, José María. Instituto de Investigaciones Químicas; España. Centro de Innovación en Química Avanzada; EspañaFil: de Gonzalo, Gonzalo. Universidad de Sevilla; EspañaMolecular Diversity Preservation International2021-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/172965Bisogno, Fabricio Román; Fernández, María del Rosario; Lassaletta, José María; de Gonzalo, Gonzalo; Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures; Molecular Diversity Preservation International; Molecules; 26; 2; 1-2021; 1-91420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/26/2/355info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules26020355info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:22:17Zoai:ri.conicet.gov.ar:11336/172965instacron: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 14:22:17.814CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures
title Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures
spellingShingle Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures
Bisogno, Fabricio Román
ASYMMETRIC CATALYSIS
ENE-TYPE REACTIONS
IONIC LIQUIDS
ORGANOCATALYSIS
SOLVENT ENGINEERING
TERTIARY ALCOHOLS
title_short Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures
title_full Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures
title_fullStr Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures
title_full_unstemmed Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures
title_sort Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures
dc.creator.none.fl_str_mv Bisogno, Fabricio Román
Fernández, María del Rosario
Lassaletta, José María
de Gonzalo, Gonzalo
author Bisogno, Fabricio Román
author_facet Bisogno, Fabricio Román
Fernández, María del Rosario
Lassaletta, José María
de Gonzalo, Gonzalo
author_role author
author2 Fernández, María del Rosario
Lassaletta, José María
de Gonzalo, Gonzalo
author2_role author
author
author
dc.subject.none.fl_str_mv ASYMMETRIC CATALYSIS
ENE-TYPE REACTIONS
IONIC LIQUIDS
ORGANOCATALYSIS
SOLVENT ENGINEERING
TERTIARY ALCOHOLS
topic ASYMMETRIC CATALYSIS
ENE-TYPE REACTIONS
IONIC LIQUIDS
ORGANOCATALYSIS
SOLVENT ENGINEERING
TERTIARY ALCOHOLS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Room temperature ionic liquids (RTILs) have been widely used as (co)solvents in several catalytic processes modifying, in most of the cases, the catalyst activity and/or the selectivity for the studied reactions. However, there are just a few examples of their use in hydrogen bonding organocatalysis. In this paper, we show the positive effect of a set of imidazole-based ionic liquids ([bmim]BF4 and [hmim]PF6 ) in the enantioselective addition of formaldehyde tert-butylhydrazone to prochiral α-keto esters catalyzed by a sugar-based chiral thiourea. Reactions performed in the presence of low percentages of RTILs led to an increase of the catalyst activity, thereby making possible to work at lower temperatures. Thus, the chiral tert-butyl azomethyl tertiary alcohols could be obtained with moderate to good conversions and higher enantioselectivities for most of the studied substrates when using up to 30 vol% of [hmim]PF6 as a cosolvent in processes performed in toluene.
Fil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Fernández, María del Rosario. Universidad de Sevilla; España
Fil: Lassaletta, José María. Instituto de Investigaciones Químicas; España. Centro de Innovación en Química Avanzada; España
Fil: de Gonzalo, Gonzalo. Universidad de Sevilla; España
description Room temperature ionic liquids (RTILs) have been widely used as (co)solvents in several catalytic processes modifying, in most of the cases, the catalyst activity and/or the selectivity for the studied reactions. However, there are just a few examples of their use in hydrogen bonding organocatalysis. In this paper, we show the positive effect of a set of imidazole-based ionic liquids ([bmim]BF4 and [hmim]PF6 ) in the enantioselective addition of formaldehyde tert-butylhydrazone to prochiral α-keto esters catalyzed by a sugar-based chiral thiourea. Reactions performed in the presence of low percentages of RTILs led to an increase of the catalyst activity, thereby making possible to work at lower temperatures. Thus, the chiral tert-butyl azomethyl tertiary alcohols could be obtained with moderate to good conversions and higher enantioselectivities for most of the studied substrates when using up to 30 vol% of [hmim]PF6 as a cosolvent in processes performed in toluene.
publishDate 2021
dc.date.none.fl_str_mv 2021-01
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/11336/172965
Bisogno, Fabricio Román; Fernández, María del Rosario; Lassaletta, José María; de Gonzalo, Gonzalo; Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures; Molecular Diversity Preservation International; Molecules; 26; 2; 1-2021; 1-9
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/172965
identifier_str_mv Bisogno, Fabricio Román; Fernández, María del Rosario; Lassaletta, José María; de Gonzalo, Gonzalo; Room temperature ionic liquids in asymmetric hetero-ene type reactions: Improving organocatalyst performance at lower temperatures; Molecular Diversity Preservation International; Molecules; 26; 2; 1-2021; 1-9
1420-3049
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.mdpi.com/1420-3049/26/2/355
info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules26020355
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
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_ 1846082621008773120
score 13.22299

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