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dc.contributor.authorRoca-López, David
dc.contributor.authorJørgensen, Karl Anker
dc.contributor.authorMerino, Pedro
dc.contributor.authorUria Pujana, Uxue
dc.contributor.authorReyes Martín, Efraim
dc.contributor.authorCarrillo Fernández, María Luisa
dc.contributor.authorVicario Hernando, José Luis
dc.date.accessioned2017-10-31T13:39:13Z
dc.date.available2017-10-31T13:39:13Z
dc.date.issued2016
dc.identifier.citationChemistry - A European Journal 22(3) : 884 – 889 (2016)es_ES
dc.identifier.issn1521-3765
dc.identifier.urihttp://hdl.handle.net/10810/23267
dc.description.abstractThe modes of catalytic action of three squaramide-derived bifunctional organocatalysts have been investigated using DFT methods. The [5+2] cycloaddition between oxidopyrilium ylides and enals has been used as model reaction. Two primary modes are possible for the different catalysts studied. The preference for one mode over the other is due to the possibility of additional favourable π,π-interactions between the H-bond activated pyrilium ylide and an electron-deficient aromatic ring bonded to a squaramide NH-group. The model can be extended to other reactions catalyzed by the same catalysts such as formal [2+2] cycloadditions between nitroalkenes and α,β-unsaturated aldehydes. The computational results are in excellent concurrence with the available experimental reports on the observed total enantioselectivity and differences in diastereoselectivity depending on the substrate and the reactiones_ES
dc.description.sponsorshipThis work was supported by Spanish MINECO Contracts CTQ2013-44367-C2-1-P (to P.M.) and CTQ2014-52107 (to J.L.V.). We also acknowledge the Government of Aragón (Spain) (Group E-10), the Basque Government (Spain) (IT328-10) and Aarhus University (Denmark) for financial support. We acknowledge the Institute of Biocomputation and Physics of Complex Systems (BIFI) at the University of Zaragoza (Spain) for computer time at clusters Terminus and Memento. D.R.-L. Thanks the Spanish Ministry of Education (MEC) for a predoctoral grant (FPU program).es_ES
dc.language.isoenges_ES
dc.publisherWiley-VCHes_ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/CTQ2013-44367-C2-1-Pes_ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/CTQ2014-52107es_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.subjectasymmetric catalysises_ES
dc.subjectdensity functionales_ES
dc.subjectcalculationses_ES
dc.subjectdienamineses_ES
dc.subjecthydrogen bondses_ES
dc.subjectpi interactionses_ES
dc.titleMechanistic Insights in the Mode of Action of Bifunctional Pyrrolidine-Squaramide-derived Organocatalystses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holder© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheimes_ES
dc.relation.publisherversionhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201504705/abstractes_ES
dc.departamentoesQuímica orgánica IIes_ES
dc.departamentoeuKimika organikoa IIes_ES


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