Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives

The first cinchona-alkaloid-organocatalyzed enantioselective synthesis of chiral 1,4-dihydropyridine derivatives is described. Bis-cinchona catalyst 3b activates the Michael addition reaction between malononitrile derivatives 2 and enamines 1, affording the appealing and highly substituted 1,4-dihyd...

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Autores: Auria-Luna, Fernando, Marqués-López, Eugenia, Gimeno, M. Concepción, Heiran, Roghayeh, Mohammadi, Somayeh, Herrera, Raquel P.
Tipo de recurso: artículo
Fecha de publicación:2017
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/155786
Acceso en línea:http://hdl.handle.net/10261/155786
Access Level:acceso abierto
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spelling Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivativesAuria-Luna, FernandoMarqués-López, EugeniaGimeno, M. ConcepciónHeiran, RoghayehMohammadi, SomayehHerrera, Raquel P.The first cinchona-alkaloid-organocatalyzed enantioselective synthesis of chiral 1,4-dihydropyridine derivatives is described. Bis-cinchona catalyst 3b activates the Michael addition reaction between malononitrile derivatives 2 and enamines 1, affording the appealing and highly substituted 1,4-dihydropyridines 4 with very good results in most cases. This is one of very few examples of the synthesis of chiral 1,4-dihydropyridines by an enantioselective catalytic procedure. The highly substituted final compounds are of interest for their potential biological activity. This efficient protocol opens the door to a new area of research for the asymmetric construction of these skeletons for which enantioselective syntheses are still very limited.Authors thank the Ministerio de Economía y Competitividad (MINECO/FEDER CTQ2016-75816-C2-1-P), the Spanish High Research Council (CSIC) (PIE-201580I010) and Gobierno de Aragon-Fondo Social Europeo (E77 and E104) for financial support of their research.Peer ReviewedAmerican Chemical SocietyMinisterio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas (España)European CommissionGobierno de AragónConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2017201720172017info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501http://hdl.handle.net/10261/155786reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-75816-C2-1-Phttps://doi.org/10.1021/acs.joc.7b00176Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1557862026-05-22T06:33:51Z
dc.title.none.fl_str_mv Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives
title Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives
spellingShingle Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives
Auria-Luna, Fernando
title_short Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives
title_full Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives
title_fullStr Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives
title_full_unstemmed Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives
title_sort Asymmetric organocatalytic synthesis of substituted chiral 1,4-dihydropyridine derivatives
dc.creator.none.fl_str_mv Auria-Luna, Fernando
Marqués-López, Eugenia
Gimeno, M. Concepción
Heiran, Roghayeh
Mohammadi, Somayeh
Herrera, Raquel P.
author Auria-Luna, Fernando
author_facet Auria-Luna, Fernando
Marqués-López, Eugenia
Gimeno, M. Concepción
Heiran, Roghayeh
Mohammadi, Somayeh
Herrera, Raquel P.
author_role author
author2 Marqués-López, Eugenia
Gimeno, M. Concepción
Heiran, Roghayeh
Mohammadi, Somayeh
Herrera, Raquel P.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Consejo Superior de Investigaciones Científicas (España)
European Commission
Gobierno de Aragón
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description The first cinchona-alkaloid-organocatalyzed enantioselective synthesis of chiral 1,4-dihydropyridine derivatives is described. Bis-cinchona catalyst 3b activates the Michael addition reaction between malononitrile derivatives 2 and enamines 1, affording the appealing and highly substituted 1,4-dihydropyridines 4 with very good results in most cases. This is one of very few examples of the synthesis of chiral 1,4-dihydropyridines by an enantioselective catalytic procedure. The highly substituted final compounds are of interest for their potential biological activity. This efficient protocol opens the door to a new area of research for the asymmetric construction of these skeletons for which enantioselective syntheses are still very limited.
publishDate 2017
dc.date.none.fl_str_mv 2017
2017
2017
2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/155786
url http://hdl.handle.net/10261/155786
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-75816-C2-1-P
https://doi.org/10.1021/acs.joc.7b00176
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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score 15,811543

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