Multicomponent Approach to Silica-Grafted Peptide Catalysts: A 3D Continuous-Flow Organocatalytic System with On-line Monitoring of Conversion and Stereoselectivity

Author(s)

Scatena, Gabriel S. ^[1] ; de la Torre, Alexander F. ^[1] ; Cass, Quezia B. ^[1] ; Rivera, Daniel G. ^{[1, 2]} ; Paixao, Marcio W. ^[1]

Affiliation

^[1] Fed Univ Sao Carlos UFSCar, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Havana, Fac Chem, Ctr Nat Prod Res, Havana 10400 - Cuba

• Document type: Journal article
• Source: CHEMCATCHEM; v. 6, n. 11, p. 3208-3214, NOV 2014.
• Web of Science Citations: 13

Abstract

The derivatization of organocatalysts with functional appendages suitable to anchor onto solid supports is usually achieved by stepwise syntheses. As an alternative to such a strategy, this work describes a one-pot approach to silylated prolyl-peptide catalysts by a multicomponent reaction that enables the simultaneous incorporation of the catalytic and the heterogenizable (triethoxysilane) moieties. A microreactor with high catalytic efficacy and reproducibly in the conjugate addition of aldehydes to nitroolefins was obtained by grafting onto HPLC-grade silica (10 mm) and packing into a column with a selected catalyst. A 3D continuous-flow system that includes the on-line monitoring of the reaction outcome was set up. For that, the microreactor was coupled to a chromatographic column for the separation of the remaining substrates from the Michael adduct in the second dimension, followed by a chiral polysaccharide column for the analysis of conversion and stereoselectivity. This approach represents a new instrumental setup that combines the advantages of multidimensional chromatography and flow catalysis. (AU)

• FAPESP's process: 13/21599-8 - Multicomponent organocatalytic strategies to anticancer natural products
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Visiting Researcher Grant - International