Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides an...

Autores
Chabour, Ihssene; Castelló, Luis M.; Mancebo Aracil, Juan; Martín Rodríguez, María; de Gracia Retamosa, María; Nájera, Carmen; Sansano, José M.
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The asymmetric 1,3-dipolar cycloaddition of an imino ester 5 with tert-butyl acrylate is catalyzed by a dual chiral silver(I) complex formed from a chiral phosphoramidite 14 and the chiral silver(I) binolphosphate (R)-17. This reaction is selected to achieve the synthesis of enantiomerically enriched key structures to access the third generation of GSK HCV inhibitors. The scope of this dual chiral catalytic system is analyzed by employing different imino esters and dipolarophiles, and also compared with the same cycloaddition reactions performed with the chiral phosphoramidite 14·AgClO4 complex.
Fil: Chabour, Ihssene. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; España
Fil: Castelló, Luis M.. Universidad de Alicante; España
Fil: Mancebo Aracil, Juan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad de Alicante; España
Fil: Martín Rodríguez, María. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; España
Fil: de Gracia Retamosa, María. Consejo Superior de Investigaciones Científicas; España. Centro de Innovación en Química Avanzada; España
Fil: Nájera, Carmen. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; España
Fil: Sansano, José M.. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; España
Materia
Enantioselective
Chiral
Cycloaddition
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/56599
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/56599
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenesChabour, IhsseneCastelló, Luis M.Mancebo Aracil, JuanMartín Rodríguez, Maríade Gracia Retamosa, MaríaNájera, CarmenSansano, José M.EnantioselectiveChiralCycloadditionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The asymmetric 1,3-dipolar cycloaddition of an imino ester 5 with tert-butyl acrylate is catalyzed by a dual chiral silver(I) complex formed from a chiral phosphoramidite 14 and the chiral silver(I) binolphosphate (R)-17. This reaction is selected to achieve the synthesis of enantiomerically enriched key structures to access the third generation of GSK HCV inhibitors. The scope of this dual chiral catalytic system is analyzed by employing different imino esters and dipolarophiles, and also compared with the same cycloaddition reactions performed with the chiral phosphoramidite 14·AgClO4 complex.Fil: Chabour, Ihssene. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; EspañaFil: Castelló, Luis M.. Universidad de Alicante; EspañaFil: Mancebo Aracil, Juan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad de Alicante; EspañaFil: Martín Rodríguez, María. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; EspañaFil: de Gracia Retamosa, María. Consejo Superior de Investigaciones Científicas; España. Centro de Innovación en Química Avanzada; EspañaFil: Nájera, Carmen. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; EspañaFil: Sansano, José M.. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; EspañaPergamon-Elsevier Science Ltd2017-10-15info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/56599Chabour, Ihssene; Castelló, Luis M.; Mancebo Aracil, Juan; Martín Rodríguez, María; de Gracia Retamosa, María; et al.; Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 28; 10; 15-10-2017; 1423-14290957-41661362-511XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0957416617303920info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2017.08.011info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:02:20Zoai:ri.conicet.gov.ar:11336/56599instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-10 13:02:20.282CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
title Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
spellingShingle Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
Chabour, Ihssene
Enantioselective
Chiral
Cycloaddition
title_short Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
title_full Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
title_fullStr Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
title_full_unstemmed Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
title_sort Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
dc.creator.none.fl_str_mv Chabour, Ihssene
Castelló, Luis M.
Mancebo Aracil, Juan
Martín Rodríguez, María
de Gracia Retamosa, María
Nájera, Carmen
Sansano, José M.
author Chabour, Ihssene
author_facet Chabour, Ihssene
Castelló, Luis M.
Mancebo Aracil, Juan
Martín Rodríguez, María
de Gracia Retamosa, María
Nájera, Carmen
Sansano, José M.
author_role author
author2 Castelló, Luis M.
Mancebo Aracil, Juan
Martín Rodríguez, María
de Gracia Retamosa, María
Nájera, Carmen
Sansano, José M.
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Enantioselective
Chiral
Cycloaddition
topic Enantioselective
Chiral
Cycloaddition
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The asymmetric 1,3-dipolar cycloaddition of an imino ester 5 with tert-butyl acrylate is catalyzed by a dual chiral silver(I) complex formed from a chiral phosphoramidite 14 and the chiral silver(I) binolphosphate (R)-17. This reaction is selected to achieve the synthesis of enantiomerically enriched key structures to access the third generation of GSK HCV inhibitors. The scope of this dual chiral catalytic system is analyzed by employing different imino esters and dipolarophiles, and also compared with the same cycloaddition reactions performed with the chiral phosphoramidite 14·AgClO4 complex.
Fil: Chabour, Ihssene. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; España
Fil: Castelló, Luis M.. Universidad de Alicante; España
Fil: Mancebo Aracil, Juan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universidad de Alicante; España
Fil: Martín Rodríguez, María. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; España
Fil: de Gracia Retamosa, María. Consejo Superior de Investigaciones Científicas; España. Centro de Innovación en Química Avanzada; España
Fil: Nájera, Carmen. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; España
Fil: Sansano, José M.. Universidad de Alicante; España. Centro de Innovación en Química Avanzada; España
description The asymmetric 1,3-dipolar cycloaddition of an imino ester 5 with tert-butyl acrylate is catalyzed by a dual chiral silver(I) complex formed from a chiral phosphoramidite 14 and the chiral silver(I) binolphosphate (R)-17. This reaction is selected to achieve the synthesis of enantiomerically enriched key structures to access the third generation of GSK HCV inhibitors. The scope of this dual chiral catalytic system is analyzed by employing different imino esters and dipolarophiles, and also compared with the same cycloaddition reactions performed with the chiral phosphoramidite 14·AgClO4 complex.
publishDate 2017
dc.date.none.fl_str_mv 2017-10-15
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/56599
Chabour, Ihssene; Castelló, Luis M.; Mancebo Aracil, Juan; Martín Rodríguez, María; de Gracia Retamosa, María; et al.; Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 28; 10; 15-10-2017; 1423-1429
0957-4166
1362-511X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/56599
identifier_str_mv Chabour, Ihssene; Castelló, Luis M.; Mancebo Aracil, Juan; Martín Rodríguez, María; de Gracia Retamosa, María; et al.; Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 28; 10; 15-10-2017; 1423-1429
0957-4166
1362-511X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0957416617303920
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2017.08.011
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1842980009658023936
score 12.993085

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