Enantioselective synthesis of a-aryl a-hydrazino phosphonates

Catalysts generated in situ by the combination of pyridine–hydrazone N,N-ligands and Pd(TFA)2 have been applied to the addition of arylboronic acids to formylphosphonate-derived hydrazones, yielding α-aryl α-hydrazino phosphonates in excellent enantioselectivities (96 → 99% ee). Subsequent removal o...

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Detalles Bibliográficos
Autores: Alberca, Saúl, Romero Parra, Javier, Fernández López, Israel, Fernández, Rosario, Lassaletta, José M., Monge, David
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/108997
Acceso en línea:https://hdl.handle.net/20.500.14352/108997
Access Level:acceso abierto
Palabra clave:547
Química orgánica (Química)
2306 Química Orgánica
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spelling Enantioselective synthesis of a-aryl a-hydrazino phosphonatesAlberca, SaúlRomero Parra, JavierFernández López, IsraelFernández, RosarioLassaletta, José M.Monge, David547Química orgánica (Química)2306 Química OrgánicaCatalysts generated in situ by the combination of pyridine–hydrazone N,N-ligands and Pd(TFA)2 have been applied to the addition of arylboronic acids to formylphosphonate-derived hydrazones, yielding α-aryl α-hydrazino phosphonates in excellent enantioselectivities (96 → 99% ee). Subsequent removal of the benzyloxycarbonyl (Cbz) N-protecting group afforded key building blocks en route to appealing artificial peptides, herbicides and antitumoral derivatives. Experimental and computational data support a stereochemical model based on aryl-palladium intermediates in which the phosphono hydrazone coordinates in its Z-configuration, maximizing the interactions between the substrate and the pyridine–hydrazone ligand.RSCUniversidad Complutense de Madrid20242024-01-0120242024-01-01journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/108997reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)InglésengAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-106358GB-C21 CATALIZADORES, LIGANDOS, METODOS Y REACTIVOS PARA SINTESIS ORGANICA SELECTIVAAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-106358GB-C22 CATALIZADORES, LIGANDOS, METODOS Y REACTIVOS PARA SINTESIS ORGANICA SELECTIVAAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-106184GB-I00 UNA APROXIMACION DIFERENTE PARA ENTENDER Y CONTROLAR LA CATALISISopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/1089972026-06-02T12:44:21Z
dc.title.none.fl_str_mv Enantioselective synthesis of a-aryl a-hydrazino phosphonates
title Enantioselective synthesis of a-aryl a-hydrazino phosphonates
spellingShingle Enantioselective synthesis of a-aryl a-hydrazino phosphonates
Alberca, Saúl
547
Química orgánica (Química)
2306 Química Orgánica
title_short Enantioselective synthesis of a-aryl a-hydrazino phosphonates
title_full Enantioselective synthesis of a-aryl a-hydrazino phosphonates
title_fullStr Enantioselective synthesis of a-aryl a-hydrazino phosphonates
title_full_unstemmed Enantioselective synthesis of a-aryl a-hydrazino phosphonates
title_sort Enantioselective synthesis of a-aryl a-hydrazino phosphonates
dc.creator.none.fl_str_mv Alberca, Saúl
Romero Parra, Javier
Fernández López, Israel
Fernández, Rosario
Lassaletta, José M.
Monge, David
author Alberca, Saúl
author_facet Alberca, Saúl
Romero Parra, Javier
Fernández López, Israel
Fernández, Rosario
Lassaletta, José M.
Monge, David
author_role author
author2 Romero Parra, Javier
Fernández López, Israel
Fernández, Rosario
Lassaletta, José M.
Monge, David
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
Química orgánica (Química)
2306 Química Orgánica
topic 547
Química orgánica (Química)
2306 Química Orgánica
description Catalysts generated in situ by the combination of pyridine–hydrazone N,N-ligands and Pd(TFA)2 have been applied to the addition of arylboronic acids to formylphosphonate-derived hydrazones, yielding α-aryl α-hydrazino phosphonates in excellent enantioselectivities (96 → 99% ee). Subsequent removal of the benzyloxycarbonyl (Cbz) N-protecting group afforded key building blocks en route to appealing artificial peptides, herbicides and antitumoral derivatives. Experimental and computational data support a stereochemical model based on aryl-palladium intermediates in which the phosphono hydrazone coordinates in its Z-configuration, maximizing the interactions between the substrate and the pyridine–hydrazone ligand.
publishDate 2024
dc.date.none.fl_str_mv 2024
2024-01-01
2024
2024-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/108997
url https://hdl.handle.net/20.500.14352/108997
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-106358GB-C21 CATALIZADORES, LIGANDOS, METODOS Y REACTIVOS PARA SINTESIS ORGANICA SELECTIVA
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-106358GB-C22 CATALIZADORES, LIGANDOS, METODOS Y REACTIVOS PARA SINTESIS ORGANICA SELECTIVA
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2019-106184GB-I00 UNA APROXIMACION DIFERENTE PARA ENTENDER Y CONTROLAR LA CATALISIS
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv RSC
publisher.none.fl_str_mv RSC
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.228081

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