First aromatic amine organocatalysed activation of α,β-unsaturated ketones

This work provides an unprecedented example of a chiral aromatic amine used to activate α,β-unsaturated ketones in asymmetric aminocatalysis. Chiral aromatic diamine VII has been efficiently employed, as a proof of concept, in the Michael addition reaction between benzylideneacetones (1a-f) and coum...

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Detalles Bibliográficos
Autores: Sonsona, Isaac G., Marqués-López, Eugenia, Gimeno, M. Concepción, Herrera, Raquel P.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2019
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/208612
Acceso en línea:http://hdl.handle.net/10261/208612
Access Level:acceso abierto
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spelling First aromatic amine organocatalysed activation of α,β-unsaturated ketonesSonsona, Isaac G.Marqués-López, EugeniaGimeno, M. ConcepciónHerrera, Raquel P.This work provides an unprecedented example of a chiral aromatic amine used to activate α,β-unsaturated ketones in asymmetric aminocatalysis. Chiral aromatic diamine VII has been efficiently employed, as a proof of concept, in the Michael addition reaction between benzylideneacetones (1a-f) and coumarins (2a-d). The reaction gives rise to warfarin derivatives 3 with promising results using this family of catalysts for the first time. The additional studies performed supported the bifunctional mode of activation of the chiral catalyst VII and the covalent nature of the interactions between the catalyst VII and benzylideneacetones 1.This work was supported by a 2018 Leonardo Grant for Researchers and Cultural Creators, BBVA Foundation. The authors also thank Ministerio de Economía, Industria y Competitividad (MINECO-FEDER CTQ2016-75816-C2-1-P and CTQ2017-88091-P), Universidad de Zaragoza (JIUZ-2017-CIE-05) and Gobierno de Aragón-Fondo Social Europeo (Research Group E07_17R) for financial support of their research. We acknowledge support of the publication fee by the CSIC Open Access Publication Support Initiative through its Unit of Information Resources for Research (URICI).Royal Society of Chemistry (UK)Fundación BBVAMinisterio de Economía y Competitividad (España)Ministerio de Ciencia, Innovación y Universidades (España)Agencia Estatal de Investigación (España)Universidad de ZaragozaGobierno de AragónEuropean CommissionConsejo Superior de Investigaciones Científicas (España)Sonsona, Isaac G.[ 0000-0001-9988-0287]Marqués-López, Eugenia [0000-0001-6832-8983]Gimeno, M. Concepción [0000-0003-0553-0695]Herrera, Raquel P. [0000-0002-5244-9569]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2020202020192020info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/208612reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##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-Pinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-88091-PCTQ2017-88091-P/AEI/10.13039/501100011033http://doi.org/10.1039/c9nj02392eSíinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2086122026-05-22T06:33:51Z
dc.title.none.fl_str_mv First aromatic amine organocatalysed activation of α,β-unsaturated ketones
title First aromatic amine organocatalysed activation of α,β-unsaturated ketones
spellingShingle First aromatic amine organocatalysed activation of α,β-unsaturated ketones
Sonsona, Isaac G.
title_short First aromatic amine organocatalysed activation of α,β-unsaturated ketones
title_full First aromatic amine organocatalysed activation of α,β-unsaturated ketones
title_fullStr First aromatic amine organocatalysed activation of α,β-unsaturated ketones
title_full_unstemmed First aromatic amine organocatalysed activation of α,β-unsaturated ketones
title_sort First aromatic amine organocatalysed activation of α,β-unsaturated ketones
dc.creator.none.fl_str_mv Sonsona, Isaac G.
Marqués-López, Eugenia
Gimeno, M. Concepción
Herrera, Raquel P.
author Sonsona, Isaac G.
author_facet Sonsona, Isaac G.
Marqués-López, Eugenia
Gimeno, M. Concepción
Herrera, Raquel P.
author_role author
author2 Marqués-López, Eugenia
Gimeno, M. Concepción
Herrera, Raquel P.
author2_role author
author
author
dc.contributor.none.fl_str_mv Fundación BBVA
Ministerio de Economía y Competitividad (España)
Ministerio de Ciencia, Innovación y Universidades (España)
Agencia Estatal de Investigación (España)
Universidad de Zaragoza
Gobierno de Aragón
European Commission
Consejo Superior de Investigaciones Científicas (España)
Sonsona, Isaac G.[ 0000-0001-9988-0287]
Marqués-López, Eugenia [0000-0001-6832-8983]
Gimeno, M. Concepción [0000-0003-0553-0695]
Herrera, Raquel P. [0000-0002-5244-9569]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description This work provides an unprecedented example of a chiral aromatic amine used to activate α,β-unsaturated ketones in asymmetric aminocatalysis. Chiral aromatic diamine VII has been efficiently employed, as a proof of concept, in the Michael addition reaction between benzylideneacetones (1a-f) and coumarins (2a-d). The reaction gives rise to warfarin derivatives 3 with promising results using this family of catalysts for the first time. The additional studies performed supported the bifunctional mode of activation of the chiral catalyst VII and the covalent nature of the interactions between the catalyst VII and benzylideneacetones 1.
publishDate 2019
dc.date.none.fl_str_mv 2019
2020
2020
2020
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/10261/208612
url http://hdl.handle.net/10261/208612
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
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info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-75816-C2-1-P
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-88091-P
CTQ2017-88091-P/AEI/10.13039/501100011033
http://doi.org/10.1039/c9nj02392e
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Royal Society of Chemistry (UK)
publisher.none.fl_str_mv Royal Society of Chemistry (UK)
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
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