Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation

An atroposelective Ir-catalyzed dynamic kinetic resolution (DKR) of 2-(quinolin-8-yl)benzaldehydes/1-naphthaldehydes by transfer hydrogenative coupling of allyl acetate is disclosed. The allylation reaction takes place with simultaneous installation of central and axial chirality, reaching high dias...

Descripción completa

Detalles Bibliográficos
Autores: Carmona, José A., Rodríguez-Salamanca, Patricia, Fernández, Rosario, Lassaletta, José M., Hornillos, Valentín
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2023
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/354736
Acceso en línea:http://hdl.handle.net/10261/354736
https://api.elsevier.com/content/abstract/scopus_id/85164952066
Access Level:acceso abierto
Palabra clave:Allylation
Asymmetric Catalysis
Axial Chirality
Iridium Catalysis
Quinolines
id ES_0fc8afe16832ef56be8a5eff94e2d5f2
oai_identifier_str oai:digital.csic.es:10261/354736
network_acronym_str ES
network_name_str España
repository_id_str
spelling Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative AllylationCarmona, José A.Rodríguez-Salamanca, PatriciaFernández, RosarioLassaletta, José M.Hornillos, ValentínAllylationAsymmetric CatalysisAxial ChiralityIridium CatalysisQuinolinesAn atroposelective Ir-catalyzed dynamic kinetic resolution (DKR) of 2-(quinolin-8-yl)benzaldehydes/1-naphthaldehydes by transfer hydrogenative coupling of allyl acetate is disclosed. The allylation reaction takes place with simultaneous installation of central and axial chirality, reaching high diastereoselectivities and excellent enantiomeric excesses when ortho-cyclometalated iridium-DM-BINAP is used as the catalyst. The racemization of the substrates occurs through a designed transient Lewis acid-base interaction between the quinoline nitrogen atom and the aldehyde carbonyl group.We thank the Spanish Ministerio de Ciencia e Innovación (Grants PID2019-106358GB-C21, PID2019-106358GB-C22, contracts RYC-2017-22294 for V.H. and BES-2017-081561 for P. R-S), European funding (ERDF), and Junta de Andalucía (Grants P18-FR-3531, P18-FR-644, US-1262867, and US-1260906). We also thank Dr. Francisco José Fernández de Córdova (IIQ-CSIC) for X-ray diffraction analysis.Peer reviewedWiley-VCHAgencia Estatal de Investigación (España)Ministerio de Ciencia y Tecnología (España)Junta de AndalucíaEuropean CommissionCarmona, José A [0000-0003-0358-7874]Rodríguez-Salamanca, Patricia [0000-0003-2212-2079]Fernández, Rosario [0000-0002-1755-1525]Lassaletta, José M. [ 0000-0003-1772-2723]Hornillos, Valentín [0000-0002-6181-9146]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202420242023info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10261/354736https://api.elsevier.com/content/abstract/scopus_id/85164952066reponame: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##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/BES-2017-081561info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-106358GB-C21info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-106358GB-C22info:eu-repo/grantAgreement/AEI//RYC-2017-22294Angewandte Chemie (International ed. in English)https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202306981Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3547362026-05-22T06:33:51Z
dc.title.none.fl_str_mv Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation
title Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation
spellingShingle Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation
Carmona, José A.
Allylation
Asymmetric Catalysis
Axial Chirality
Iridium Catalysis
Quinolines
title_short Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation
title_full Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation
title_fullStr Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation
title_full_unstemmed Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation
title_sort Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation
dc.creator.none.fl_str_mv Carmona, José A.
Rodríguez-Salamanca, Patricia
Fernández, Rosario
Lassaletta, José M.
Hornillos, Valentín
author Carmona, José A.
author_facet Carmona, José A.
Rodríguez-Salamanca, Patricia
Fernández, Rosario
Lassaletta, José M.
Hornillos, Valentín
author_role author
author2 Rodríguez-Salamanca, Patricia
Fernández, Rosario
Lassaletta, José M.
Hornillos, Valentín
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Agencia Estatal de Investigación (España)
Ministerio de Ciencia y Tecnología (España)
Junta de Andalucía
European Commission
Carmona, José A [0000-0003-0358-7874]
Rodríguez-Salamanca, Patricia [0000-0003-2212-2079]
Fernández, Rosario [0000-0002-1755-1525]
Lassaletta, José M. [ 0000-0003-1772-2723]
Hornillos, Valentín [0000-0002-6181-9146]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Allylation
Asymmetric Catalysis
Axial Chirality
Iridium Catalysis
Quinolines
topic Allylation
Asymmetric Catalysis
Axial Chirality
Iridium Catalysis
Quinolines
description An atroposelective Ir-catalyzed dynamic kinetic resolution (DKR) of 2-(quinolin-8-yl)benzaldehydes/1-naphthaldehydes by transfer hydrogenative coupling of allyl acetate is disclosed. The allylation reaction takes place with simultaneous installation of central and axial chirality, reaching high diastereoselectivities and excellent enantiomeric excesses when ortho-cyclometalated iridium-DM-BINAP is used as the catalyst. The racemization of the substrates occurs through a designed transient Lewis acid-base interaction between the quinoline nitrogen atom and the aldehyde carbonyl group.
publishDate 2023
dc.date.none.fl_str_mv 2023
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/354736
https://api.elsevier.com/content/abstract/scopus_id/85164952066
url http://hdl.handle.net/10261/354736
https://api.elsevier.com/content/abstract/scopus_id/85164952066
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#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/BES-2017-081561
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-106358GB-C21
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-106358GB-C22
info:eu-repo/grantAgreement/AEI//RYC-2017-22294
Angewandte Chemie (International ed. in English)
https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202306981
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
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
_version_ 1869403473462689792
score 15.81155

Similares en LA Referencia