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

Autor(es)

de la Torre, Alexander F. ^[1] ; Scatena, Gabriel S. ^[2] ; Valdes, Oscar ^[3] ; Rivera, Daniel G. ^[4] ; Paixao, Marcia W. ^[2]

Afiliação do(s) autor(es)

^[1] Univ Concepcion, Fac Ciencias Quim, Dept Quim Organ, Edmundo Larenas 234 Interior Casilla 160-C, Concepcion - Chile

^[2] Univ Fed Sao Carlos, Dept Quim, BR-97105900 Sao Carlos, SP - Brazil

^[3] Univ Catolica Maule, Vicerrectoria Invest & Postgrad, Talca 3460000 - Chile

^[4] Univ Havana, Fac Chem, Ctr Nat Prod Res, Havana 10400 - Cuba

• Tipo de documento: Artigo Científico
• Fonte: Beilstein Journal of Organic Chemistry; v. 15, p. 1210-1216, JUN 4 2019.
• Citações Web of Science: 1

Resumo

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 beta-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. (AU)

• Processo FAPESP: 15/17141-1 - Desenvolvimento e Estudos Mecanísticos de Novas Metodologias Sintéticas para Síntese de Compostos Bioativos
• Beneficiário: Ricardo Samuel Schwab
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia