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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
de la Torre, Alexander F. [1] ; Scatena, Gabriel S. [2] ; Valdes, Oscar [3] ; Rivera, Daniel G. [4] ; Paixao, Marcia W. [2]
Total Authors: 5
Affiliation:
[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
Total Affiliations: 4
Document type: Journal article
Source: Beilstein Journal of Organic Chemistry; v. 15, p. 1210-1216, JUN 4 2019.
Web of Science Citations: 1
Abstract

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)

FAPESP's process: 15/17141-1 - Development and Mechanism Studies of New Synthetic Methodologies for the Synthesis of Bioactive Compounds.
Grantee:Ricardo Samuel Schwab
Support Opportunities: Regular Research Grants
FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support Opportunities: Research Grants - Research Centers in Engineering Program