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Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds

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dc.contributor.author Fernández Wang, Martí
dc.contributor.author Parera Briansó, Magda
dc.contributor.author Parella Coll, Teodor
dc.contributor.author Lledó Ponsati, Agustí
dc.contributor.author Le Bras, Jean
dc.contributor.author Muzart, Jacques
dc.contributor.author Pla i Quintana, Anna
dc.contributor.author Roglans i Ribas, Anna
dc.date.issued 2016-06-02
dc.identifier.issn 1615-4150 (versió paper)
dc.identifier.issn 1615-4169 (versió electrònica)
dc.identifier.uri http://hdl.handle.net/10256/13146
dc.description.abstract A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84-97%) through a kinetic resolution of the M-B-H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels-Alder cycloadducts in good yields cat
dc.description.sponsorship Financial support from the Spanish Ministry of Education and Science (MINECO) (Projects No.: CTQ2014-54306-P, CTQ2012-32436 and a RyC contract to A. L.) and the DIUE of the Generalitat de Catalunya (Project No.: 2014SGR931) are acknowledged cat
dc.format.mimetype application/pdf cat
dc.language.iso eng cat
dc.publisher Wiley cat
dc.relation MINECO/PE 2015-2017/CTQ2014-54306-P cat
dc.relation AGAUR/2014-2016/2014 SGR-931 cat
dc.relation.isformatof Reproducció digital del document publicat a: http://dx.doi.org/10.1002/adsc.201600039 cat
dc.relation.ispartof © Advanced Synthesis and Catalysis, 2016, vol. 358, núm. 11, p. 1848-1853 cat
dc.relation.ispartofseries Articles publicats (D-Q) cat
dc.rights Tots els drets reservats cat
dc.subject Reaccions d'addició cat
dc.subject Addition reactions cat
dc.subject Catàlisi cat
dc.subject Catalysis cat
dc.subject Catalitzadors de rodi cat
dc.subject Rhodium catalyst cat
dc.subject Rodi cat
dc.subject Rhodium cat
dc.title Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds cat
dc.type info:eu-repo/semantics/article cat
dc.rights.accessRights info:eu-repo/semantics/closedAccess cat
dc.embargo.terms Cap cat
dc.type.version info:eu-repo/semantics/publishedVersion cat
dc.identifier.doi http://dx.doi.org/10.1002/adsc.201600039
dc.contributor.funder Ministerio de Economía y Competitividad (Espanya) cat
dc.contributor.funder Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca cat


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