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Interlocking the Catalyst: Thread versus Rotaxane-Mediated Enantiodivergent Michael Addition of Ketones to beta-Nitrostyrene

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dc.contributor.authorMartinez-Cuezva, Alberto
dc.contributor.authorMarin-Luna, Marta
dc.contributor.authorAlonso, Diego A.
dc.contributor.authorRos-Ñiguez, Diego
dc.contributor.authorAlajarín, Mateo
dc.contributor.authorBerná Cánovas, José
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2021-02-01T18:28:20Z
dc.date.available2021-02-01T18:28:20Z
dc.date.created2019
dc.date.issued2019-06-19
dc.description.abstractFumaramide threads bearing one l-prolinamide fragment have been designed as templates for promoting the efficient formation of novel Leigh’s [2]rotaxanes. Both threads and rotaxanes are shown to catalyze the asymmetric addition of ketones to β-nitrostyrene in an enantio- and diastereoselective manner. Interestingly, the enantioselective course of these processes is reversed simply by changing from thread to rotaxane as catalyst. DFT computations have allowed to rationalize the stereodivergence shown by the interlocked and noninterlocked catalysts.es
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dc.format.extent5es
dc.identifier.doi10.1021/acs.orglett.9b01791
dc.identifier.issn1523-7060
dc.identifier.issn1523-7052
dc.identifier.urihttp://hdl.handle.net/10201/102341
dc.languageenges
dc.publisherAmerican Chemical Societyes
dc.relationThis work was supported by the MINECO (CTQ2017-87231-P and CTQ2015-66624-P) with joint financing by FEDER Funds and Fundación Seneca-CARM (Project 20811/PI/18). A.M.-C. thanks MICINN for a Ramon y Cajal contract and funding (RYC-2017-22700). M.M.L. thanks Xunta de Galicia for her postdoctoral contract (ED418B 2016/166-0).es
dc.relation.isreplacedbyhttps://doi.org/10.1021/acs.orglett.9b01791es
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.orglett.9b01791es
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución-NoComercial-SinDerivadas 3.0 España*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/*
dc.subjectOrganocatalysises
dc.subjectAsymmetric Synthesises
dc.subjectRotaxaneses
dc.subjectMechanical Bond Effectses
dc.subjectDFT calculationses
dc.subject.otherCDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánicaes
dc.titleInterlocking the Catalyst: Thread versus Rotaxane-Mediated Enantiodivergent Michael Addition of Ketones to beta-Nitrostyrenees
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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