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

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.

Automated summary

In this study, a library of N-alkylated lipopeptide organocatalysts were synthesized through an isocyanide-based multicomponent reaction. These catalysts were evaluated in the 1,4-addition of aldehydes to trans-beta-nitrostyrene using water as the sole solvent, resulting in excellent yields, diastereoselectivities, and enantioselectivities under sustainable reaction conditions with low catalyst loadings and without additives.