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dc.contributor.authorRodríguez Llansola, Francisco
dc.contributor.authorMiravet, Juan
dc.contributor.authorEscuder, Beatriu
dc.date.accessioned2012-11-08T15:48:35Z
dc.date.available2012-11-08T15:48:35Z
dc.date.issued2010
dc.identifier.citationChemistry - A European Journal (2010), 16, 28, p. 8480–8486ca_CA
dc.identifier.issn0947-6539
dc.identifier.urihttp://hdl.handle.net/10234/51440
dc.description.abstractL-Proline-L-valine dipeptide derivatives, which self-assemble in toluene, have been studied as stereoselective catalysts in the conjugate addition of cyclohexanone to trans-β-nitrostyrene. Remarkable effects on the stereoselectivity are observed associated to the aggregation of the catalyst. Outstanding differences were observed between the catalytic activity of compound 1, which forms supramolecular gels in toluene, and compound 2, which is not a gelator. In the former case, the enantioselectivity of the reaction was almost insensitive to changes in catalyst concentration and temperature, but in the case of compound 2, the catalytic activity was very much affected by those variables. Structural studies indicate that the results can be rationalized by taking into account significant conformational changes experienced by the catalytic L-proline derivatives associated with the aggregation process. The results highlight that catalyst self-assembly is a very important issue to consider in the stereoselective outcome of organocatalytic reactions. Especially relevant is the fact that the use of supramolecular gels as organocatalyts emerges as a technique that affords reliable and constant stereoselectivity in different conditions with the added value of easy catalyst recovery.ca_CA
dc.format.extent6 p.ca_CA
dc.language.isoengca_CA
dc.publisherWiley-VCHca_CA
dc.rightsCopyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheimca_CA
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/*
dc.subjectgelsca_CA
dc.subjectorganocatalysisca_CA
dc.subjectprolineca_CA
dc.subjectself-assemblyca_CA
dc.subjectsupramolecular chemistryca_CA
dc.titleSupramolecular Catalysis with Extended Aggregates and Gels: Inversion of Stereoselectivity Caused by Self-Assemblyca_CA
dc.typeinfo:eu-repo/semantics/articleca_CA
dc.identifier.doihttp://dx.doi.org/10.1002/chem.201000654
dc.rights.accessRightsinfo:eu-repo/semantics/restrictedAccessca_CA
dc.relation.publisherVersionhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201000654/abstractca_CA


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