Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reaction

This is the peer reviewed version of the following article: Angewandte Chemie - International Edition 60.9 (2021): 4555-4560, which has been published in final form at https://doi.org/10.1002/anie.202013020. This article may be used for non-commercial purposes in accordance with Wiley Terms and Cond...

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Detalles Bibliográficos
Autores: Rodríguez, Ricardo I., Mollari, Leonardo, Alemán Lara, José Julián
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/699583
Acceso en línea:http://hdl.handle.net/10486/699583
https://dx.doi.org/10.1002/anie.202013020
Access Level:acceso abierto
Palabra clave:Enantioselectivity
Hydrogen-atom transfer
Photocatalysis
Pyrrolines
Radical–radical coupling
Química
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spelling Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reactionRodríguez, Ricardo I.Mollari, LeonardoAlemán Lara, José JuliánEnantioselectivityHydrogen-atom transferPhotocatalysisPyrrolinesRadical–radical couplingQuímicaThis is the peer reviewed version of the following article: Angewandte Chemie - International Edition 60.9 (2021): 4555-4560, which has been published in final form at https://doi.org/10.1002/anie.202013020. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibitedHerein, a light-driven, atom-economical process that provides access to enantiomerically enriched substituted chiral 1-pyrroline derivatives is introduced. The strategy involves the distal functionalization of acyl heterocycles through a hydrogen-atom transfer (HAT) process and the use of tailor-made ketimines as reliable electrophilic partners. This transformation is translated into an enantiomerically controlled radical/polar cascade reaction in which water is produced as the sole by-product and stereoselectivity is dictated by coordination to a chiral-at-rhodium catalystFinancial support was provided by the European Research Council (ERC-CoG, contract number: 647550, 861930), Spanish Government (RTI2018-095038-B-I00), “Comunidadde Madrid” and European Structural Funds (S2018/NMT-4367)WileyDepartamento de Química OrgánicaFacultad de Ciencias20212021-01-12research articlehttp://purl.org/coar/resource_type/c_2df8fbb1AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/699583https://dx.doi.org/10.1002/anie.202013020reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengEuropean Commission http://dx.doi.org/10.13039/501100000780 Horizon 2020 Framework Programme 647550European Commission http://dx.doi.org/10.13039/501100000780 Horizon 2020 Framework Programme 861930open accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/6995832026-06-23T12:46:27Z
dc.title.none.fl_str_mv Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reaction
title Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reaction
spellingShingle Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reaction
Rodríguez, Ricardo I.
Enantioselectivity
Hydrogen-atom transfer
Photocatalysis
Pyrrolines
Radical–radical coupling
Química
title_short Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reaction
title_full Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reaction
title_fullStr Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reaction
title_full_unstemmed Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reaction
title_sort Light-driven enantioselective synthesis of pyrroline derivatives by a radical/polar cascade reaction
dc.creator.none.fl_str_mv Rodríguez, Ricardo I.
Mollari, Leonardo
Alemán Lara, José Julián
author Rodríguez, Ricardo I.
author_facet Rodríguez, Ricardo I.
Mollari, Leonardo
Alemán Lara, José Julián
author_role author
author2 Mollari, Leonardo
Alemán Lara, José Julián
author2_role author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv Enantioselectivity
Hydrogen-atom transfer
Photocatalysis
Pyrrolines
Radical–radical coupling
Química
topic Enantioselectivity
Hydrogen-atom transfer
Photocatalysis
Pyrrolines
Radical–radical coupling
Química
description This is the peer reviewed version of the following article: Angewandte Chemie - International Edition 60.9 (2021): 4555-4560, which has been published in final form at https://doi.org/10.1002/anie.202013020. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited
publishDate 2021
dc.date.none.fl_str_mv 2021
2021-01-12
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/10486/699583
https://dx.doi.org/10.1002/anie.202013020
url http://hdl.handle.net/10486/699583
https://dx.doi.org/10.1002/anie.202013020
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv European Commission http://dx.doi.org/10.13039/501100000780 Horizon 2020 Framework Programme 647550
European Commission http://dx.doi.org/10.13039/501100000780 Horizon 2020 Framework Programme 861930
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
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