Synthesis of N-alkylated lipopeptides and their application as organocatalysts in asymmetric Michael addition in aqueous environments

Author(s)

Delgado, Jose A. C. ^[1] ; Vicente, Fidel E. M. ^{[1, 2]} ; de la Torre, Alexander F. ^[3] ; Fernandes, Vitor A. ^[1] ; Correa, Arlene G. ^[1] ; Paixao, Marcio W. ^[1]

Affiliation

^[1] Fed Univ Sao Carlos UFSCar, Ctr Excellence Res Sustainable Chem CERSusChem, Dept Chem, Rodovia Washington Luis, Km 235, SP-310, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Havana, Fac Chem, Dept Gen Chem, Havana - Cuba

^[3] Univ Concepcion, Fac Ciencias Quim, Dept Quim Organ, Concepcion - Chile

• Document type: Journal article
• Source: NEW JOURNAL OF CHEMISTRY; v. 45, n. 31 JUL 2021.
• Web of Science Citations: 0

Abstract

A library of N-alkylated lipopeptide organocatalysts were synthesized through an isocyanide-based multicomponent reaction. Various structural motifs were tunably introduced on the catalyst backbone with the aim of incorporating amphiphilic features. Consequently, they have further been evaluated in the 1,4-addition of aldehydes to trans-beta-nitrostyrene having water as the sole solvent. Under sustainable reaction conditions, Michael adducts were obtained in excellent yields, diastereoselectivities, and enantioselectivities using low catalyst loadings and without additives. (AU)

• 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
• FAPESP's process: 19/01973-9 - Exploration of the Asymmetric Induction in Ugi Variations Aiming the Stereoselective Synthesis and Functionalizationof N-Heterocycles
• Grantee: Vitor Alcantara Fernandes da Silva
• Support Opportunities: Scholarships in Brazil - Doctorate