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dc.contributor.CRUESPUNIVERSIDADE DE ESTADUAL DE CAMPINASpt_BR
dc.typeArtigo de periódicopt_BR
dc.titleIntermolecular Noncovalent Hydroxy-directed Enantioselective Heck Desymmetrization Of Cyclopentenol: Computationally Driven Synthesis Of Highly Functionalized Cis-4-arylcyclopentenol Scaffoldspt_BR
unicamp.author.email1967jrgomes@gmail.compt_BR
unicamp.authorNeves, J.d.S., Universidade Estadual de Campinas Faculdade de Odontologia de Piracicaba Piracicaba Brazilpt_BR
unicamp.authorNovaes, P.D., Universidade Estadual de Campinas Faculdade de Odontologia de Piracicaba Piracicaba Brazilpt_BR
unicamp.author.externalGomes, J.R., DEBIOGEM Ponta Grossa Brazilpt
unicamp.author.externalOmar, N.F., UEPG-DEBIOGEM Ponta Grossa Brazilpt
dc.description.abstractNew computationally driven protocols for the Heck desymmetrization of 3-cyclopenten-1-ol with aryldiazonium tetrafluoroborates were developed. These new conditions furnished remarkable product selectivity originating from a resident hydroxyl group and the critical choice of the reaction solvent. Mechanistic insights gleaned from theoretical calculations of the putative transition states predicted toluene as an adequate solvent choice to attain high enantioselectivity by strengthening the noncovalent interaction of the substrate hydroxyl group and the chiral cationic palladium catalyst. Laboratory experiments validated the theoretical predictions, and by employing 2% MeOH/toluene as solvent, the Heck-Matsuda reaction provided exclusively the cis-4-arylcyclopentenols 3a-l in good to excellent yields in enantiomeric excesses up to 99%. The performance of the new PyOx ligand (S)-4-tert-butyl-2-(3,5-dichloropyridin-2-yl)-4,5-dihydrooxazole was also successfully evaluated in the Heck-Matsuda desymmetrization of 3-cyclopenten-1-ol. The synthetic potential of these highly functionalized cis-4-arylcyclopentenols is illustrated by a gold-catalyzed synthesis of cyclopenta[b]benzofuran skeletons. © 2016 American Chemical Society.en
dc.relation.ispartofJournal of Organic Chemistrypt_BR
dc.publisherAmerican Chemical Societypt_BR
dc.date.issued2016pt_BR
dc.identifier.citationJournal Of Organic Chemistry. American Chemical Society, v. 81, p. 2010 - 2018, 2016.pt_BR
dc.language.isoenpt_BR
dc.description.volume81pt_BR
dc.description.issuenumberpt_BR
dc.description.firstpage2010pt_BR
dc.description.lastpage2018pt_BR
dc.rightsfechadopt_BR
dc.sourceScopuspt_BR
dc.identifier.issn00223263pt_BR
dc.identifier.doi10.1021/acs.joc.5b02846pt_BR
dc.identifier.urlhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-84960152983&partnerID=40&md5=4cb37e7a778b10c470ae06741e357975pt_BR
dc.description.sponsorshipCAPES, Fundação de Amparo à Pesquisa do Estado de São Paulopt_BR
dc.description.sponsorshipCNPq, Fundação de Amparo à Pesquisa do Estado de São Paulopt_BR
dc.description.sponsorship2011/23832-6, FAPESP, Fundação de Amparo à Pesquisa do Estado de São Paulopt_BR
dc.description.sponsorship2013/ 04813-6, FAPESP, Fundação de Amparo à Pesquisa do Estado de São Paulopt_BR
dc.description.sponsorship2013/00544-0, FAPESP, Fundação de Amparo à Pesquisa do Estado de São Paulopt_BR
dc.description.sponsorship2013/07600-3, FAPESP, Fundação de Amparo à Pesquisa do Estado de São Paulopt_BR
dc.description.sponsorship2013/25639-4, FAPESP, Fundação de Amparo à Pesquisa do Estado de São Paulopt_BR
dc.description.sponsorship2015/01491-3, FAPESP, Fundação de Amparo à Pesquisa do Estado de São Paulopt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorship1Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)pt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorship1Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)pt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.date.available2016-12-06T17:44:21Z-
dc.date.accessioned2016-12-06T17:44:21Z-
dc.description.provenanceMade available in DSpace on 2016-12-06T17:44:21Z (GMT). No. of bitstreams: 1 2-s2.0-84960152983.pdf: 2078391 bytes, checksum: 42e0a63ce24f635e98cf8eb9254ba59e (MD5) Previous issue date: 2016en
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/319552-
dc.identifier.idScopus2-s2.0-84960152983pt_BR
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