Catalytic Enantioselective Cloke–Wilson Rearrangement

Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor-acceptor cyclopropane substrate by the chiral Brønsted acid catalyst to promote the...

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Detalhes bibliográficos
Autores: Ortega Altonaga, Alesandere, Manzano, Rubén, Uria Pujana, Uxue, Carrillo Fernández, María Luisa, Reyes Martín, Efraim, Tejero, Tomás, Merino, Pedro, Vicario Hernando, José Luis
Formato: artículo
Fecha de publicación:2018
País:España
Recursos:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/63263
Acesso em linha:http://hdl.handle.net/10810/63263
Access Level:acceso abierto
Palavra-chave:asymmetric catalysis
carbocations
organocatalysis
earrangement
strainedmolecules
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spelling Catalytic Enantioselective Cloke–Wilson RearrangementOrtega Altonaga, AlesandereManzano, RubénUria Pujana, UxueCarrillo Fernández, María LuisaReyes Martín, EfraimTejero, TomásMerino, PedroVicario Hernando, José Luisasymmetric catalysiscarbocationsorganocatalysisearrangementstrainedmoleculesRacemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor-acceptor cyclopropane substrate by the chiral Brønsted acid catalyst to promote the ring-opening event, thus generating a carbocationic intermediate that subsequently undergoes cyclization. Computational studies and control experiments support this mechanistic pathway.Spanish MINECO(FEDER-CTQ2017-83633-P and FEDER-CTQ2016-76155R), BasqueGovernment(IT908-16),UPV/EHU (fellowshipto A.O.), and Government of Aragón (Grupos de Referencia,E34-R17). BIFI-ZCAM(Universidad de Zaragoza, Spain)Wiley-VCH202320232018info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/63263reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MINECO/CTQ2017-83633-P/info:eu-repo/grantAgreement/MINECO/CTQ2016-76155-R/https://onlinelibrary.wiley.com/doi/10.1002/anie.201804614https://doi.org/10.1002/anie.201804614info:eu-repo/semantics/openAccess© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheimoai:addi.ehu.eus:10810/632632026-06-18T09:23:17Z
dc.title.none.fl_str_mv Catalytic Enantioselective Cloke–Wilson Rearrangement
title Catalytic Enantioselective Cloke–Wilson Rearrangement
spellingShingle Catalytic Enantioselective Cloke–Wilson Rearrangement
Ortega Altonaga, Alesandere
asymmetric catalysis
carbocations
organocatalysis
earrangement
strainedmolecules
title_short Catalytic Enantioselective Cloke–Wilson Rearrangement
title_full Catalytic Enantioselective Cloke–Wilson Rearrangement
title_fullStr Catalytic Enantioselective Cloke–Wilson Rearrangement
title_full_unstemmed Catalytic Enantioselective Cloke–Wilson Rearrangement
title_sort Catalytic Enantioselective Cloke–Wilson Rearrangement
dc.creator.none.fl_str_mv Ortega Altonaga, Alesandere
Manzano, Rubén
Uria Pujana, Uxue
Carrillo Fernández, María Luisa
Reyes Martín, Efraim
Tejero, Tomás
Merino, Pedro
Vicario Hernando, José Luis
author Ortega Altonaga, Alesandere
author_facet Ortega Altonaga, Alesandere
Manzano, Rubén
Uria Pujana, Uxue
Carrillo Fernández, María Luisa
Reyes Martín, Efraim
Tejero, Tomás
Merino, Pedro
Vicario Hernando, José Luis
author_role author
author2 Manzano, Rubén
Uria Pujana, Uxue
Carrillo Fernández, María Luisa
Reyes Martín, Efraim
Tejero, Tomás
Merino, Pedro
Vicario Hernando, José Luis
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv asymmetric catalysis
carbocations
organocatalysis
earrangement
strainedmolecules
topic asymmetric catalysis
carbocations
organocatalysis
earrangement
strainedmolecules
description Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor-acceptor cyclopropane substrate by the chiral Brønsted acid catalyst to promote the ring-opening event, thus generating a carbocationic intermediate that subsequently undergoes cyclization. Computational studies and control experiments support this mechanistic pathway.
publishDate 2018
dc.date.none.fl_str_mv 2018
2023
2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/63263
url http://hdl.handle.net/10810/63263
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MINECO/CTQ2017-83633-P/
info:eu-repo/grantAgreement/MINECO/CTQ2016-76155-R/
https://onlinelibrary.wiley.com/doi/10.1002/anie.201804614
https://doi.org/10.1002/anie.201804614
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
eu_rights_str_mv openAccess
rights_invalid_str_mv © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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:Addi. Archivo Digital para la Docencia y la Investigación
instname:Universidad del País Vasco
instname_str Universidad del País Vasco
reponame_str Addi. Archivo Digital para la Docencia y la Investigación
collection Addi. Archivo Digital para la Docencia y la Investigación
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869423232498532352
score 15,300724

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