Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives

Producción Científica

Detalles Bibliográficos
Autores: Gil Ordóñez, Marta, Aubry, Camille, Niño, Cristopher, Maestro Fernández, Alicia, Andrés García, José María
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Institución:Universidad de Valladolid
Repositorio:UVaDOC. Repositorio Documental de la Universidad de Valladolid
OAI Identifier:oai:uvadoc.uva.es:10324/56004
Acceso en línea:https://doi.org/10.3390/molecules27206983
https://uvadoc.uva.es/handle/10324/56004
Access Level:acceso abierto
Palabra clave:Organocatalysis
Organocatálisis
Ketimines
Cetiminas
Pyrazolone
Pirazolona
id ES_dc79ea770e5fc907cd4d6c6f11d01338
oai_identifier_str oai:uvadoc.uva.es:10324/56004
network_acronym_str ES
network_name_str España
repository_id_str
spelling Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivativesGil Ordóñez, MartaAubry, CamilleNiño, CristopherMaestro Fernández, AliciaAndrés García, José MaríaOrganocatalysisOrganocatálisisKetiminesCetiminasPyrazolonePirazolonaProducción CientíficaA series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in enantioselective Mannich reactions with different 1,3-dicarbonyl compounds. This method provides a direct pathway to access the 4-amino-5-pyrazolone derivatives bearing a quaternary substituted stereocenter and containing two privileged structure motifs, the β-diketone and pyrazolinone substructures. The adducts were obtained in excellent yields (up to 90%) and enantioselectivities (up to 94:6 er) by employing a very low loading of 2 mol% of a quinine-derived bifunctional squaramide as an organocatalyst for a wide range of substrates. In addition, the utility of the obtained products was demonstrated through one step transformations to enantioenriched diheterocyclic systems (4-pyrazolyl-pyrazolone and 4-isoxazolyl-pyrazolone), potentially promising candidates for drug discovery.MDPI2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://doi.org/10.3390/molecules27206983https://uvadoc.uva.es/handle/10324/56004reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolidinstname:Universidad de ValladolidIngléshttps://www.mdpi.com/1420-3049/27/20/6983info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/oai:uvadoc.uva.es:10324/560042026-06-13T12:44:47Z
dc.title.none.fl_str_mv Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
title Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
spellingShingle Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
Gil Ordóñez, Marta
Organocatalysis
Organocatálisis
Ketimines
Cetiminas
Pyrazolone
Pirazolona
title_short Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
title_full Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
title_fullStr Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
title_full_unstemmed Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
title_sort Squaramide-catalyzed asymmetric Mannich reaction between 1,3-dicarbonyl compounds and pyrazolinone ketimines: A pathway to enantioenriched 4-pyrazolyl- and 4-isoxazolyl-4-aminopyrazolone derivatives
dc.creator.none.fl_str_mv Gil Ordóñez, Marta
Aubry, Camille
Niño, Cristopher
Maestro Fernández, Alicia
Andrés García, José María
author Gil Ordóñez, Marta
author_facet Gil Ordóñez, Marta
Aubry, Camille
Niño, Cristopher
Maestro Fernández, Alicia
Andrés García, José María
author_role author
author2 Aubry, Camille
Niño, Cristopher
Maestro Fernández, Alicia
Andrés García, José María
author2_role author
author
author
author
dc.subject.none.fl_str_mv Organocatalysis
Organocatálisis
Ketimines
Cetiminas
Pyrazolone
Pirazolona
topic Organocatalysis
Organocatálisis
Ketimines
Cetiminas
Pyrazolone
Pirazolona
description Producción Científica
publishDate 2022
dc.date.none.fl_str_mv 2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://doi.org/10.3390/molecules27206983
https://uvadoc.uva.es/handle/10324/56004
url https://doi.org/10.3390/molecules27206983
https://uvadoc.uva.es/handle/10324/56004
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://www.mdpi.com/1420-3049/27/20/6983
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolid
instname:Universidad de Valladolid
instname_str Universidad de Valladolid
reponame_str UVaDOC. Repositorio Documental de la Universidad de Valladolid
collection UVaDOC. Repositorio Documental de la Universidad de Valladolid
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869421772172951552
score 15,301603

Similares en LA Referencia