Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process

An array of enantioenriched vinyl boronates bearing an allylic carbonate moiety have been prepared through selective hydroboration of propargyl carbonates. Treatment of these vinyl boronates with TBAF in THF affords enantioenriched 1,3-disubstituted allenes through a novel 1,2-anti elimination in go...

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Detalhes bibliográficos
Autores: Jarava-Barrera, Carlos, Parra, Alejandro, Quesada, Sergio, Orgaz-Gordillo, Sergio, Fernández de la Pradilla, Roberto, Viso, Alma, Teresa, Javier, Alonso, Inés, Tortosa, Mariola
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/395544
Acesso em linha:http://hdl.handle.net/10261/395544
https://api.elsevier.com/content/abstract/scopus_id/85177649840
Access Level:acceso abierto
Palavra-chave:1,2-anti-elimination
Allenes
Boronates
Propargylic carbonates
TBAF
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spelling Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination ProcessJarava-Barrera, CarlosParra, AlejandroQuesada, SergioOrgaz-Gordillo, SergioFernández de la Pradilla, RobertoViso, AlmaTeresa, JavierAlonso, InésTortosa, Mariola1,2-anti-eliminationAllenesBoronatesPropargylic carbonatesTBAFAn array of enantioenriched vinyl boronates bearing an allylic carbonate moiety have been prepared through selective hydroboration of propargyl carbonates. Treatment of these vinyl boronates with TBAF in THF affords enantioenriched 1,3-disubstituted allenes through a novel 1,2-anti elimination in good yields and high enantiospecificities.We thank MINECO (CTQ2016-78779-R) and MICINN (PID2019-107380GB I00) for financial support. We acknowl- edge Dr. Josefina Perles (UAM) for X-ray structure analysisPeer reviewedWiley-VCHMinisterio de Economía y Competitividad (España)Ministerio de Ciencia e Innovación (España)Fernández de la Pradilla, Roberto [0000-0002-6633-8499]Viso, Alma [0000-0003-2622-4777]Tortosa, Mariola [0000-0002-5107-0549]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202520252024info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10261/395544https://api.elsevier.com/content/abstract/scopus_id/85177649840reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI//CTQ2016-78779-Rinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-107380GB-I00Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3955442026-05-22T06:33:51Z
dc.title.none.fl_str_mv Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process
title Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process
spellingShingle Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process
Jarava-Barrera, Carlos
1,2-anti-elimination
Allenes
Boronates
Propargylic carbonates
TBAF
title_short Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process
title_full Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process
title_fullStr Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process
title_full_unstemmed Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process
title_sort Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process
dc.creator.none.fl_str_mv Jarava-Barrera, Carlos
Parra, Alejandro
Quesada, Sergio
Orgaz-Gordillo, Sergio
Fernández de la Pradilla, Roberto
Viso, Alma
Teresa, Javier
Alonso, Inés
Tortosa, Mariola
author Jarava-Barrera, Carlos
author_facet Jarava-Barrera, Carlos
Parra, Alejandro
Quesada, Sergio
Orgaz-Gordillo, Sergio
Fernández de la Pradilla, Roberto
Viso, Alma
Teresa, Javier
Alonso, Inés
Tortosa, Mariola
author_role author
author2 Parra, Alejandro
Quesada, Sergio
Orgaz-Gordillo, Sergio
Fernández de la Pradilla, Roberto
Viso, Alma
Teresa, Javier
Alonso, Inés
Tortosa, Mariola
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Ministerio de Ciencia e Innovación (España)
Fernández de la Pradilla, Roberto [0000-0002-6633-8499]
Viso, Alma [0000-0003-2622-4777]
Tortosa, Mariola [0000-0002-5107-0549]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv 1,2-anti-elimination
Allenes
Boronates
Propargylic carbonates
TBAF
topic 1,2-anti-elimination
Allenes
Boronates
Propargylic carbonates
TBAF
description An array of enantioenriched vinyl boronates bearing an allylic carbonate moiety have been prepared through selective hydroboration of propargyl carbonates. Treatment of these vinyl boronates with TBAF in THF affords enantioenriched 1,3-disubstituted allenes through a novel 1,2-anti elimination in good yields and high enantiospecificities.
publishDate 2024
dc.date.none.fl_str_mv 2024
2025
2025
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/10261/395544
https://api.elsevier.com/content/abstract/scopus_id/85177649840
url http://hdl.handle.net/10261/395544
https://api.elsevier.com/content/abstract/scopus_id/85177649840
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI//CTQ2016-78779-R
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-107380GB-I00
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 Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
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
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.81155

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