Highly stereoselective modifications of peptidesvia Pd-catalyzed allylic alkylation of internal peptideamide enolates

Abstract

Pd-catalyzed allylations are excellent tools for stereoselective peptide modifications, showing several advantages compared to normal alkylations. Reactions of internal peptide amide enolates with Pd–allyl complexes proceed not only with high yields of up to 86%, they show also high regio- and diastereoselectivities (88–99%), giving rise to the trans-configured products. Therefore, this protocol is a powerful synthetic tool for the synthesis of natural product and drug molecules.