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Atroposelective Synthesis of 2-(Quinolin-8-yl)benzyl Alcohols by Biocatalytic Dynamic Kinetic Resolutions

dc.creatorCoto Cid, Juan Manueles
dc.creatorGonzalo Calvo, Gonzalo dees
dc.creatorCarmona, José A.es
dc.creatorIglesias Sigüenza, Francisco Javieres
dc.creatorRodríguez Salamanca, Patriciaes
dc.creatorFernández Fernández, Rosario Fátimaes
dc.creatorHornillos, Valentínes
dc.creatorLassaletta, José M.es
dc.date.accessioned2024-06-14T11:43:50Z
dc.date.available2024-06-14T11:43:50Z
dc.date.issued2023-12-22
dc.identifier.citationCoto Cid, J.M., Gonzalo Calvo, G.d., Carmona, J.A., Iglesias Sigüenza, F.J., Rodríguez Salamanca, P., Fernández Fernández, R.F.,...,Lassaletta, J.M. (2023). Atroposelective Synthesis of 2-(Quinolin-8-yl)benzyl Alcohols by Biocatalytic Dynamic Kinetic Resolutions. Advanced Synthesis & Catalysis, 366 (4), 909-915. https://doi.org/10.1002/adsc.202301310.
dc.identifier.issn1615-4150es
dc.identifier.issn1615-4169es
dc.identifier.urihttps://hdl.handle.net/11441/160538
dc.description.abstractA highly enantioselective biocatalytic dynamic kinetic resolution (DKR) of 2-(quinoline-8-yl) 3-methylbenzaldehydes and 1-naphthaldehydes is described. The reaction proceeds by atroposelective carbonyl reduction catalyzed by commercial ketoreductases (KREDs), generally reaching high conversions and excellent enantiomeric excesses. Both atropoisomers of the final alcohols can be obtained by a proper selection of the biocatalyst. The DKR strategy relies in the racemization of the stereogenic axis that takes place thanks to a transient Lewis acid-base interaction (LABI) between the nitrogen in the quinoline and the carbonyl group.es
dc.description.sponsorshipMinisterio de Ciencia e Innovación de España - PID2019-106358GB−C21 y PID2019-106358GB−C22es
dc.description.sponsorshipFondos europeos FEDER y Junta de Andalucía - P18-FR-3531, P18-FR-644, US-1262867 y US-1260906es
dc.formatapplication/pdfes
dc.format.extent7 p.es
dc.language.isoenges
dc.publisherWileyes
dc.relation.ispartofAdvanced Synthesis & Catalysis, 366 (4), 909-915.
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectAxial chiralityes
dc.subjectAsymmetric catalysises
dc.subjectKetoreductaseses
dc.subjectDynamic kinetic resolutiones
dc.subjectQuinolineses
dc.titleAtroposelective Synthesis of 2-(Quinolin-8-yl)benzyl Alcohols by Biocatalytic Dynamic Kinetic Resolutionses
dc.typeinfo:eu-repo/semantics/articlees
dc.type.versioninfo:eu-repo/semantics/publishedVersiones
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses
dc.contributor.affiliationUniversidad de Sevilla. Departamento de Química orgánicaes
dc.relation.projectIDPID2019-106358GB−C21es
dc.relation.projectIDPID2019-106358GB−C22es
dc.relation.projectIDP18-FR-3531es
dc.relation.projectIDP18-FR-644es
dc.relation.projectIDUS-1262867es
dc.relation.projectIDUS-1260906es
dc.relation.publisherversionhttps://doi.org/10.1002/adsc.202301310es
dc.identifier.doi10.1002/adsc.202301310es
dc.journaltitleAdvanced Synthesis & Catalysises
dc.publication.volumen366es
dc.publication.issue4es
dc.publication.initialPage909es
dc.publication.endPage915es
dc.contributor.funderMinisterio de Ciencia e Innovación (MICIN). Españaes
dc.contributor.funderEuropean Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER)es
dc.contributor.funderJunta de Andalucíaes

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