First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives

This article belongs to the Special Issue Stereogenic Centers.

Detalles Bibliográficos
Autores: Auria-Luna, Fernando, Marqués-López, Eugenia, Herrera, Raquel P.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/186589
Acceso en línea:http://hdl.handle.net/10261/186589
Access Level:acceso abierto
Palabra clave:Chiral base
1,4-dihydropyridine
Enantioselective
Hydrazone
Organocatalysis
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spelling First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivativesAuria-Luna, FernandoMarqués-López, EugeniaHerrera, Raquel P.Chiral base1,4-dihydropyridineEnantioselectiveHydrazoneOrganocatalysisThis article belongs to the Special Issue Stereogenic Centers.Preliminary results concerning the first asymmetric synthesis of highly functionalized 1-benzamido-1,4-dihydropyridine derivatives via the reaction of hydrazones with alkylidenemalononitriles in the presence of β-isocupreidine catalyst are reported. The moderate, but promising, enantioselectivity observed (40–54% ee), opens the door to a new area of research for the asymmetric construction of new chiral 1,4-dihydropyridine derivatives, whose enantioselective catalytic preparation are still very limited. Moreover, the use of hydrazones for the enantioselective construction of chiral 1,4-dihydropyridines has been overlooked in the literature so far. Therefore, our research represents a pivotal example in this field which remains still unexplored.This research was funded by Ministerio de Economía, Industria y Competitividad [CTQ2017-88091-P], Universidad de Zaragoza [JIUZ-2017-CIE-05] and Gobierno de Aragón-Fondo Social Europeo [Research Group E07_17R].Peer reviewedMultidisciplinary Digital Publishing InstituteMinisterio de Economía, Industria y Competitividad (España)Agencia Estatal de Investigación (España)Universidad de ZaragozaGobierno de AragónEuropean CommissionMarqués-López, Eugenia [0000-0001-6832-8983]Herrera, Raquel P. [0000-0002-5244-9569]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201920192018info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/186589reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#CTQ2017-88091-P/AEI/10.13039/501100011033info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-88091-Phttps://doi.org/10.3390/molecules23102692Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1865892026-05-22T06:33:51Z
dc.title.none.fl_str_mv First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives
title First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives
spellingShingle First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives
Auria-Luna, Fernando
Chiral base
1,4-dihydropyridine
Enantioselective
Hydrazone
Organocatalysis
title_short First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives
title_full First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives
title_fullStr First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives
title_full_unstemmed First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives
title_sort First organocatalytic asymmetric synthesis of 1-benzamido-1,4-dihydropyridine derivatives
dc.creator.none.fl_str_mv Auria-Luna, Fernando
Marqués-López, Eugenia
Herrera, Raquel P.
author Auria-Luna, Fernando
author_facet Auria-Luna, Fernando
Marqués-López, Eugenia
Herrera, Raquel P.
author_role author
author2 Marqués-López, Eugenia
Herrera, Raquel P.
author2_role author
author
dc.contributor.none.fl_str_mv Ministerio de Economía, Industria y Competitividad (España)
Agencia Estatal de Investigación (España)
Universidad de Zaragoza
Gobierno de Aragón
European Commission
Marqués-López, Eugenia [0000-0001-6832-8983]
Herrera, Raquel P. [0000-0002-5244-9569]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Chiral base
1,4-dihydropyridine
Enantioselective
Hydrazone
Organocatalysis
topic Chiral base
1,4-dihydropyridine
Enantioselective
Hydrazone
Organocatalysis
description This article belongs to the Special Issue Stereogenic Centers.
publishDate 2018
dc.date.none.fl_str_mv 2018
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/186589
url http://hdl.handle.net/10261/186589
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
CTQ2017-88091-P/AEI/10.13039/501100011033
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-88091-P
https://doi.org/10.3390/molecules23102692
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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