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...

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Autores: Carmona, José A., Rodríguez-Salamanca, Patricia, Fernández, Rosario, Lassaletta, José M., Hornillos, Valentín
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2023
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/354736
Acesso em linha:http://hdl.handle.net/10261/354736
https://api.elsevier.com/content/abstract/scopus_id/85164952066
Access Level:acceso abierto
Palavra-chave:Allylation
Asymmetric Catalysis
Axial Chirality
Iridium Catalysis
Quinolines
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spelling Dynamic Kinetic Resolution of 2-(Quinolin-8-yl)Benzaldehydes: Atroposelective Iridium-Catalyzed Transfer Hydrogenative Allylation Carmona, José A. Rodríguez-Salamanca, Patricia Fernández, Rosario Lassaletta, José M. Hornillos, Valentín Allylation Asymmetric Catalysis Axial Chirality Iridium Catalysis Quinolines 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. 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 reviewed Wiley-VCH http://hdl.handle.net/10261/354736 https://api.elsevier.com/content/abstract/scopus_id/85164952066
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
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
topic Allylation
Asymmetric Catalysis
Axial Chirality
Iridium Catalysis
Quinolines
topic_facet 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
format article
status_str acceptedVersion
url http://hdl.handle.net/10261/354736
https://api.elsevier.com/content/abstract/scopus_id/85164952066
eu_rights_str_mv openAccess
publisher Wiley-VCH
institution Consejo Superior de Investigaciones Científicas (CSIC)
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
_version_ 1878431520939573248
publishDateSort 2023
author_browse Carmona, José A.
Fernández, Rosario
Hornillos, Valentín
Lassaletta, José M.
Rodríguez-Salamanca, Patricia
publisherStr Wiley-VCH
score 6.924472

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