Ugi reaction-derived prolyl peptide catalysts grafted on the renewable polymer polyfurfuryl alcohol for applications in heterogeneous enamine catalysis

Autor: Alexander F. de la Torre, Gabriel S. Scatena, Oscar Valdés, Daniel G. Rivera, Márcio W. Paixão
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 15, Iss 1, Pp 1210-1216 (2019)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.15.118
Popis: The multicomponent synthesis of prolyl pseudo-peptide catalysts using the Ugi reaction with furfurylamines or isocyanides is described. The incorporation of such a polymerizable furan handle enabled the subsequent polymerization of the peptide catalyst with furfuryl alcohol, thus rendering polyfurfuryl alcohol-supported catalysts for applications in heterogeneous enamine catalysis. The utilization of the polymer-supported catalysts in both batch and continuous-flow organocatalytic procedures proved moderate catalytic efficacy and enantioselectivity, but excellent diastereoselectivity in the asymmetric Michael addition of n-butanal to β-nitrostyrene that was used as a model reaction. This work supports the potential of multicomponent reactions towards the assembly of catalysts and their simultaneous functionalization for immobilization.
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