Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates

A copper-catalyzed enantioselective cyclopropanation involving trifluorodiazoethane in the presence of alkenyl boronates has been developed. This transformation enables the preparation of 2-substituted-3-(trifluoromethyl)cyclopropylboronates with high levels of stereocontrol. The products are valuab...

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Autores: Altarejos Salido, Julia|||0000-0002-2871-8597, Sucunza Sáenz, David|||0000-0002-3307-4204, Vaquero López, Juan José|||0000-0002-3820-9673, Carreras Pérez Aradros, Javier|||0000-0002-1521-6758
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universidad de Alcalá (UAH)
Repositorio:e_Buah Biblioteca Digital Universidad de Alcalá
Idioma:inglés
OAI Identifier:oai:ebuah.uah.es:10017/49328
Acceso en línea:http://hdl.handle.net/10017/49328
https://dx.doi.org/10.1021/acs.orglett.1c02420
Access Level:acceso abierto
Palabra clave:(Trifluoromethyl)cyclopropylboronates
Enantioselective cyclopropanation
Trifluorodiazoethane
Alkenyl boronates
Copper catalysis
Trifluoromethylcyclopropanes
Química
Chemistry
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spelling Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-CyclopropylboronatesAltarejos Salido, Julia|||0000-0002-2871-8597Sucunza Sáenz, David|||0000-0002-3307-4204Vaquero López, Juan José|||0000-0002-3820-9673Carreras Pérez Aradros, Javier|||0000-0002-1521-6758(Trifluoromethyl)cyclopropylboronatesEnantioselective cyclopropanationTrifluorodiazoethaneAlkenyl boronatesCopper catalysisTrifluoromethylcyclopropanesQuímicaChemistryA copper-catalyzed enantioselective cyclopropanation involving trifluorodiazoethane in the presence of alkenyl boronates has been developed. This transformation enables the preparation of 2-substituted-3-(trifluoromethyl)cyclopropylboronates with high levels of stereocontrol. The products are valuable synthetic intermediates by transformation of the boronate group. This methodology can be applied to the synthesis of novel trifluoromethylated analogues of trans-2-arylcyclopropylamines, which are prevalent motifs in biologically active compounds.Universidad de AlcaláMinisterio de Economía y CompetitividadMinisterio de Ciencia e InnovaciónComunidad de MadridAgencia Estatal de Investigación20212021-07-2820212021-07-2820222022-07-28journal articlehttp://purl.org/coar/resource_type/c_6501NAhttp://purl.org/coar/version/c_be7fb7dd8ff6fe43info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10017/49328https://dx.doi.org/10.1021/acs.orglett.1c02420reponame:e_Buah Biblioteca Digital Universidad de Alcaláinstname:Universidad de Alcalá (UAH)InglésengUAH Proyectos para potenciar la creación y consolidación de grupos de investigación CCG19 ESAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 CTQ2017-85263-R Azaheterociclos y azaborinos: aplicaciones como compuestos bioactivos en la enfermedad renal, tinción celular y bioimagenMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Not available RD16%2F0009%2F0015 Red de Investigación RenalMinisterio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available PID2019-105007GAI00Comunidad de Madrid http://dx.doi.org/10.13039/100012818 Not available CM%2FJIN%2F2019-025 Nuevos compuestos organoborados con subestructuras de interés en química médicaopen 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:ebuah.uah.es:10017/493282026-06-18T11:13:07Z
dc.title.none.fl_str_mv Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
spellingShingle Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
Altarejos Salido, Julia|||0000-0002-2871-8597
(Trifluoromethyl)cyclopropylboronates
Enantioselective cyclopropanation
Trifluorodiazoethane
Alkenyl boronates
Copper catalysis
Trifluoromethylcyclopropanes
Química
Chemistry
title_short Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title_full Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title_fullStr Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title_full_unstemmed Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
title_sort Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates
dc.creator.none.fl_str_mv Altarejos Salido, Julia|||0000-0002-2871-8597
Sucunza Sáenz, David|||0000-0002-3307-4204
Vaquero López, Juan José|||0000-0002-3820-9673
Carreras Pérez Aradros, Javier|||0000-0002-1521-6758
author Altarejos Salido, Julia|||0000-0002-2871-8597
author_facet Altarejos Salido, Julia|||0000-0002-2871-8597
Sucunza Sáenz, David|||0000-0002-3307-4204
Vaquero López, Juan José|||0000-0002-3820-9673
Carreras Pérez Aradros, Javier|||0000-0002-1521-6758
author_role author
author2 Sucunza Sáenz, David|||0000-0002-3307-4204
Vaquero López, Juan José|||0000-0002-3820-9673
Carreras Pérez Aradros, Javier|||0000-0002-1521-6758
author2_role author
author
author
dc.subject.none.fl_str_mv (Trifluoromethyl)cyclopropylboronates
Enantioselective cyclopropanation
Trifluorodiazoethane
Alkenyl boronates
Copper catalysis
Trifluoromethylcyclopropanes
Química
Chemistry
topic (Trifluoromethyl)cyclopropylboronates
Enantioselective cyclopropanation
Trifluorodiazoethane
Alkenyl boronates
Copper catalysis
Trifluoromethylcyclopropanes
Química
Chemistry
description A copper-catalyzed enantioselective cyclopropanation involving trifluorodiazoethane in the presence of alkenyl boronates has been developed. This transformation enables the preparation of 2-substituted-3-(trifluoromethyl)cyclopropylboronates with high levels of stereocontrol. The products are valuable synthetic intermediates by transformation of the boronate group. This methodology can be applied to the synthesis of novel trifluoromethylated analogues of trans-2-arylcyclopropylamines, which are prevalent motifs in biologically active compounds.
publishDate 2021
dc.date.none.fl_str_mv 2021
2021-07-28
2021
2021-07-28
2022
2022-07-28
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
NA
http://purl.org/coar/version/c_be7fb7dd8ff6fe43
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10017/49328
https://dx.doi.org/10.1021/acs.orglett.1c02420
url http://hdl.handle.net/10017/49328
https://dx.doi.org/10.1021/acs.orglett.1c02420
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv UAH Proyectos para potenciar la creación y consolidación de grupos de investigación CCG19 ES
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 CTQ2017-85263-R Azaheterociclos y azaborinos: aplicaciones como compuestos bioactivos en la enfermedad renal, tinción celular y bioimagen
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Not available RD16%2F0009%2F0015 Red de Investigación Renal
Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available PID2019-105007GAI00
Comunidad de Madrid http://dx.doi.org/10.13039/100012818 Not available CM%2FJIN%2F2019-025 Nuevos compuestos organoborados con subestructuras de interés en química médica
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.source.none.fl_str_mv reponame:e_Buah Biblioteca Digital Universidad de Alcalá
instname:Universidad de Alcalá (UAH)
instname_str Universidad de Alcalá (UAH)
reponame_str e_Buah Biblioteca Digital Universidad de Alcalá
collection e_Buah Biblioteca Digital Universidad de Alcalá
repository.name.fl_str_mv
repository.mail.fl_str_mv
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