Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides

This is the peer reviewed version of the following article: Chemistry – A European Journal 22.14 (2016): 4952 - 4959, which has been published in final form at http://doi.org/10.1002/chem.201504869. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions fo...

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Autores: Ponce, Alberto, Alonso Montero, María Inés, Adrio Sevilla, Francisco Javier, Carretero Gonzálvez, Juan Carlos
Tipo de recurso: artículo
Fecha de publicación:2016
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/685956
Acceso en línea:http://hdl.handle.net/10486/685956
https://dx.doi.org/10.1002/chem.201504869
Access Level:acceso abierto
Palabra clave:asymmetric catalysis
cycloaddition
fluorinated pyrrolidines
silver
ylides
Química
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spelling Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine YlidesPonce, AlbertoAlonso Montero, María InésAdrio Sevilla, Francisco JavierCarretero Gonzálvez, Juan Carlosasymmetric catalysiscycloadditionfluorinated pyrrolidinessilverylidesQuímicaThis is the peer reviewed version of the following article: Chemistry – A European Journal 22.14 (2016): 4952 - 4959, which has been published in final form at http://doi.org/10.1002/chem.201504869. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived VersionsA silver-catalyzed 1,3-dipolar cycloaddition of fluorinated azomethine ylides and activated olefins is reported. The reaction offers a straightforward and atom-economical procedure for the preparation of fluorinated pyrrolidines. Broad scope and high levels of diastereoselectivity have been achieved simply by using AgOAc/PPh3as the catalyst system. The high efficiency of the cycloaddition relies on the presence of a metal-coordinating group on the imine moiety, such as an ester or heteroaryl group. The asymmetric version of the cycloaddition has been developed by using Taniaphos as a chiral ligandFinancial support of this work by the Ministerio de Economía y Competitividad (MINECO, CTQ2012-35790) is gratefully acknowledgedWileyDepartamento de Química OrgánicaFacultad de Ciencias20162016-03-24research articlehttp://purl.org/coar/resource_type/c_2df8fbb1AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/685956https://dx.doi.org/10.1002/chem.201504869reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/6859562026-06-23T12:46:27Z
dc.title.none.fl_str_mv Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides
title Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides
spellingShingle Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides
Ponce, Alberto
asymmetric catalysis
cycloaddition
fluorinated pyrrolidines
silver
ylides
Química
title_short Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides
title_full Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides
title_fullStr Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides
title_full_unstemmed Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides
title_sort Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides
dc.creator.none.fl_str_mv Ponce, Alberto
Alonso Montero, María Inés
Adrio Sevilla, Francisco Javier
Carretero Gonzálvez, Juan Carlos
author Ponce, Alberto
author_facet Ponce, Alberto
Alonso Montero, María Inés
Adrio Sevilla, Francisco Javier
Carretero Gonzálvez, Juan Carlos
author_role author
author2 Alonso Montero, María Inés
Adrio Sevilla, Francisco Javier
Carretero Gonzálvez, Juan Carlos
author2_role author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv asymmetric catalysis
cycloaddition
fluorinated pyrrolidines
silver
ylides
Química
topic asymmetric catalysis
cycloaddition
fluorinated pyrrolidines
silver
ylides
Química
description This is the peer reviewed version of the following article: Chemistry – A European Journal 22.14 (2016): 4952 - 4959, which has been published in final form at http://doi.org/10.1002/chem.201504869. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions
publishDate 2016
dc.date.none.fl_str_mv 2016
2016-03-24
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/685956
https://dx.doi.org/10.1002/chem.201504869
url http://hdl.handle.net/10486/685956
https://dx.doi.org/10.1002/chem.201504869
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
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
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300724

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