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

Beilstein Journal of Organic Chemistry

Daniel G. Rivera¹  Alexander F. de la Torre²  Márcio W. Paixão³  Gabriel S. Scatena³  Oscar Valdés⁴ 

[1] Center for Natural Products Research, Faculty of Chemistry, University of Havana, Zapata y G, 10400, La Habana, Cuba;Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Concepción, Edmundo Larenas 234-interior-Casilla 160-C-Concepción, Chile;Márcio W. Paixão, Departamento de Química, Universidade Federal de São Carlos, São Carlos, SP, 97105-900, Brazil;Vicerrectoria de Investigación y Postgrado, Universidad Católica del Maule, Talca 3460000, Chile;

关键词: flow chemistry;    heterogeneous catalysis;    multicomponent reactions;    organocatalysis;    polyfurfuryl alcohol;   

DOI  :  10.3762/bjoc.15.118

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown