DUGiDocsA Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
dc.contributor.author
dc.date.accessioned
2019-09-16T08:33:50Z
dc.date.available
2021-04-07T08:03:01Z
dc.date.issued
2019-07-11
dc.identifier.issn
1523-7060
dc.identifier.uri
dc.description.abstract
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
dc.description.sponsorship
We 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.V
dc.format.extent
6 p.
dc.format.mimetype
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society (ACS)
dc.relation
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-P/ES/AVANCES EN LA REACTIVIDAD DE FULLERENOS Y NANOTUBOS: ESTUDIOS TEORICO-EXPERIMENTALES DE CICLACIONES CATALIZADAS POR METALES DE TRANSICION/
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-83587-P/ES/CATALISIS BIOMIMETICA DE CICLACIONES CARBOCATIONICAS CON RECEPTORES SINTETICOS/
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Versió popstprint del document publicat a: https://doi.org/10.1021/acs.orglett.9b02032
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© Organic Letters, 2019, vol. 21, núm. 17, p. 6608-6613
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Articles publicats (D-Q)
dc.rights
Tots els drets reservats
dc.source
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
dc.subject
dc.title
A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.embargo.terms
2020-07-11T00:00:00Z
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2020-07-11
dc.type.version
info:eu-repo/semantics/acceptedVersion
dc.identifier.doi
dc.identifier.idgrec
030145
dc.contributor.funder
dc.type.peerreviewed
peer-reviewed
dc.relation.FundingProgramme
dc.relation.ProjectAcronym
dc.identifier.eissn
1523-7052