Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis

A straightforward methodology for the enantioselective synthesis of 1,2-dihydrophthalazines via dearomatization of phthalazines by anion-binding catalysis has been developed. The process involves the Mannich-type addition of silyl ketene acetals to in situ generated N-acylphthalazinium chlorides usi...

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Detalhes bibliográficos
Autores: Velázquez, Marta, Fernández, Rosario, Lassaletta, José M., Monge, David
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2023
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositório:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/353963
Acesso em linha:http://hdl.handle.net/10261/353963
https://api.elsevier.com/content/abstract/scopus_id/85179608058
Access Level:Acceso aberto
Palavra-chave:Asymetric
Phthalazines
Anion-Binding
Catalysis
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spelling Asymmetric Dearomatization of Phthalazines by Anion-Binding CatalysisVelázquez, MartaFernández, RosarioLassaletta, José M.Monge, DavidAsymetricPhthalazinesAnion-BindingCatalysisA straightforward methodology for the enantioselective synthesis of 1,2-dihydrophthalazines via dearomatization of phthalazines by anion-binding catalysis has been developed. The process involves the Mannich-type addition of silyl ketene acetals to in situ generated N-acylphthalazinium chlorides using a tert-leucine derived thiourea as a H-bond donor catalyst. Ensuing selective and high-yielding transformations provide appealing dihydro- and tetrahydro-phthalazines, phthalazones, and piperazic acid homologues, en route to biologically relevant molecules.We thank the Spanish MICINN(grantsPID2019-106358GB-C21,PID2019-106358GB-C22,and PID2022-137888NB-I00),European FEDER funds, and the Junta de Andalucía(grants P18-FR-3531,P18-FR-644,and US-1262867)for financial support.We also thank Dr. Francisco José Fernández de Córdova (IIQ-CSIC) for X-ray structure analysisPeer reviewedACS PublicationsJunta de AndalucíaMinisterio de Ciencia e Innovación (España)Agencia Estatal de Investigación (España)Velázquez, Marta [0000-0002-4350-4968]Fernández, Rosario [0000-0002-1755-1525]Lassaletta, José M.[0000-0003-1772-2723]Monge, David [0000-0001-8007-4111]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202420242023info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10261/353963https://api.elsevier.com/content/abstract/scopus_id/85179608058reponame: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/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/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-137888NB-I00https://pubs.acs.org/doi/epdf/10.1021/acs.orglett.3c03325Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3539632026-05-22T06:33:51Z
dc.title.none.fl_str_mv Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis
title Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis
spellingShingle Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis
Velázquez, Marta
Asymetric
Phthalazines
Anion-Binding
Catalysis
title_short Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis
title_full Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis
title_fullStr Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis
title_full_unstemmed Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis
title_sort Asymmetric Dearomatization of Phthalazines by Anion-Binding Catalysis
dc.creator.none.fl_str_mv Velázquez, Marta
Fernández, Rosario
Lassaletta, José M.
Monge, David
author Velázquez, Marta
author_facet Velázquez, Marta
Fernández, Rosario
Lassaletta, José M.
Monge, David
author_role author
author2 Fernández, Rosario
Lassaletta, José M.
Monge, David
author2_role author
author
author
dc.contributor.none.fl_str_mv Junta de Andalucía
Ministerio de Ciencia e Innovación (España)
Agencia Estatal de Investigación (España)
Velázquez, Marta [0000-0002-4350-4968]
Fernández, Rosario [0000-0002-1755-1525]
Lassaletta, José M.[0000-0003-1772-2723]
Monge, David [0000-0001-8007-4111]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Asymetric
Phthalazines
Anion-Binding
Catalysis
topic Asymetric
Phthalazines
Anion-Binding
Catalysis
description A straightforward methodology for the enantioselective synthesis of 1,2-dihydrophthalazines via dearomatization of phthalazines by anion-binding catalysis has been developed. The process involves the Mannich-type addition of silyl ketene acetals to in situ generated N-acylphthalazinium chlorides using a tert-leucine derived thiourea as a H-bond donor catalyst. Ensuing selective and high-yielding transformations provide appealing dihydro- and tetrahydro-phthalazines, phthalazones, and piperazic acid homologues, en route to biologically relevant molecules.
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
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/353963
https://api.elsevier.com/content/abstract/scopus_id/85179608058
url http://hdl.handle.net/10261/353963
https://api.elsevier.com/content/abstract/scopus_id/85179608058
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
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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/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-137888NB-I00
https://pubs.acs.org/doi/epdf/10.1021/acs.orglett.3c03325
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 ACS Publications
publisher.none.fl_str_mv ACS Publications
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
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