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Preparation of chitosan-supported urea materials and their application in some organocatalytic procedures

AutorGonzalo, Gonzalo de; Franconetti, A.; Fernández, Rosario; Lassaletta, José M. ; Cabrera-Escribano, Francisca
Palabras claveChitosan-supported ureas
Cyanosilylation
Organocatalysis
DFT calculations
Heterogeneous catalysis
Chiral tertiary alcohols
Fecha de publicación2018
EditorPergamon Press
CitaciónCarbohydrate Polymers 199: 365- 374 (2018)
ResumenAn efficient and mild procedure was developed for the preparation of three chitosan-supported ureas containing electron-withdrawing groups. These catalysts were characterized and employed as organocatalysts in different transformations, including the enantioselective cyanosilylation of α-ketoesters and aldehydes, the asymmetric addition of formaldehyde tert-butyl hydrazone to prochiral α-ketoesters and a Friedel-Crafts reaction. Several parameters that can affect the activity and selectivity of the reactions were analysed. The supported catalysts can be reused for more than 10 cycles with only a small loss in their properties. Finally, theoretical DFT calculations were carried out to interpret the results of the catalysed reactions.
URIhttp://hdl.handle.net/10261/173222
Identificadoresdoi: 10.1016/j.carbpol.2018.07.009
issn: 0144-8617
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