A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles

A novel methodology to transform bisallenes into a variety of polycyclic derivatives employing rhodium(I) catalysis has been developed. This transformation encompasses an intramolecular Rh-catalyzed cycloisomerization of bisallenes 1 to deliver a reac-tive cycloheptadiene, which concomitantly underg...

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Autores: Artigas Ruf, Albert, Vila Vadrí, Jordi, Lledó Ponsati, Agustí, Solà i Puig, Miquel, Pla i Quintana, Anna, Roglans i Ribas, Anna
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/16953
Acceso en línea:http://hdl.handle.net/10256/16953
Access Level:acceso abierto
Palabra clave:Compostos policíclics
Isomerització
Teoria del funcional de densitat
Polycyclic compounds
Isomerization
Density functionals
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spelling A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic HeterocyclesArtigas Ruf, AlbertVila Vadrí, JordiLledó Ponsati, AgustíSolà i Puig, MiquelPla i Quintana, AnnaRoglans i Ribas, AnnaCompostos policíclicsIsomeritzacióTeoria del funcional de densitatPolycyclic compoundsIsomerizationDensity functionalsA novel methodology to transform bisallenes into a variety of polycyclic derivatives employing rhodium(I) catalysis has been developed. This transformation encompasses an intramolecular Rh-catalyzed cycloisomerization of bisallenes 1 to deliver a reac-tive cycloheptadiene, which concomitantly undergoes a regioselective [4+2] cycloaddition with alkenes. A complete mechanistic study of this transformation has been undertaken including DFT calculations. Overall, the methodology presented here constitutes a new and straightforward entry to polycyclic dihydroazepine and dihydrooxepine derivatives employing catalytic methodsWe are grateful for the financial support by the Spanish Ministry of Economy and Competitivity (MINECO) (Projects CTQ2017- 85341-P and CTQ2017-83587-P, FI predoctoral grant to A.A., RyC contract RYC2012-11112 to A.L.), the Generalitat de Catalunya (Project 2017-SGR-39, Xarxa de Referència en Química Teòrica i Computacional, ICREA Academia 2014 prize for M.S.) and UdG for IF predoctoral grant to J.VAmerican Chemical Society (ACS)Ministerio de Economía y Competitividad (Espanya)info2019info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionpeer-reviewed6 p.application/pdfhttp://hdl.handle.net/10256/16953http://hdl.handle.net/10256/16953© Organic Letters, 2019, vol. 21, núm. 17, p. 6608-6613Articles publicats (D-Q)Artigas Ruf, Albert Vila, Jordi Lledó Ponsati, Agustí Solà i Puig, Miquel Pla i Quintana, Anna Roglans i Ribas, Anna 2019 A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles Organic Letters 21 17 6608 6613reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.orglett.9b02032info:eu-repo/semantics/altIdentifier/issn/1523-7060info:eu-repo/semantics/altIdentifier/eissn/1523-7052info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-Pinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-83587-PTots els drets reservatsinfo:eu-repo/semantics/openAccessoai:recercat.cat:10256/169532026-05-29T05:05:01Z
dc.title.none.fl_str_mv A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
title A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
spellingShingle A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
Artigas Ruf, Albert
Compostos policíclics
Isomerització
Teoria del funcional de densitat
Polycyclic compounds
Isomerization
Density functionals
title_short A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
title_full A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
title_fullStr A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
title_full_unstemmed A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
title_sort A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
dc.creator.none.fl_str_mv Artigas Ruf, Albert
Vila Vadrí, Jordi
Lledó Ponsati, Agustí
Solà i Puig, Miquel
Pla i Quintana, Anna
Roglans i Ribas, Anna
author Artigas Ruf, Albert
author_facet Artigas Ruf, Albert
Vila Vadrí, Jordi
Lledó Ponsati, Agustí
Solà i Puig, Miquel
Pla i Quintana, Anna
Roglans i Ribas, Anna
author_role author
author2 Vila Vadrí, Jordi
Lledó Ponsati, Agustí
Solà i Puig, Miquel
Pla i Quintana, Anna
Roglans i Ribas, Anna
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (Espanya)
dc.subject.none.fl_str_mv Compostos policíclics
Isomerització
Teoria del funcional de densitat
Polycyclic compounds
Isomerization
Density functionals
topic Compostos policíclics
Isomerització
Teoria del funcional de densitat
Polycyclic compounds
Isomerization
Density functionals
description A novel methodology to transform bisallenes into a variety of polycyclic derivatives employing rhodium(I) catalysis has been developed. This transformation encompasses an intramolecular Rh-catalyzed cycloisomerization of bisallenes 1 to deliver a reac-tive cycloheptadiene, which concomitantly undergoes a regioselective [4+2] cycloaddition with alkenes. A complete mechanistic study of this transformation has been undertaken including DFT calculations. Overall, the methodology presented here constitutes a new and straightforward entry to polycyclic dihydroazepine and dihydrooxepine derivatives employing catalytic methods
publishDate 2019
dc.date.none.fl_str_mv 2019
info
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
peer-reviewed
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/16953
http://hdl.handle.net/10256/16953
url http://hdl.handle.net/10256/16953
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.orglett.9b02032
info:eu-repo/semantics/altIdentifier/issn/1523-7060
info:eu-repo/semantics/altIdentifier/eissn/1523-7052
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-P
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-83587-P
dc.rights.none.fl_str_mv Tots els drets reservats
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Tots els drets reservats
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 6 p.
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society (ACS)
publisher.none.fl_str_mv American Chemical Society (ACS)
dc.source.none.fl_str_mv © Organic Letters, 2019, vol. 21, núm. 17, p. 6608-6613
Articles publicats (D-Q)
Artigas Ruf, Albert Vila, Jordi Lledó Ponsati, Agustí Solà i Puig, Miquel Pla i Quintana, Anna Roglans i Ribas, Anna 2019 A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles Organic Letters 21 17 6608 6613
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,228081

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