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

Autor(es)

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]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: NEW JOURNAL OF CHEMISTRY; v. 45, n. 31 JUL 2021.
• Citações Web of Science: 0

Resumo

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)

• 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
• Processo FAPESP: 19/01973-9 - Exploração da Indução Assimétrica em Variações da Reação de Ugi Visando a Síntese e Funcionalização Estereosseletiva de Sistemas Heterocíclicos Nitrogenados
• Beneficiário: Vitor Alcantara Fernandes da Silva
• Modalidade de apoio: Bolsas no Brasil - Doutorado