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

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-β-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.