A Highly Stereoselective Synthesis of the Functionalized (E)-Alkene Dipeptide Isostere of Trp-Val via Organocyanocopper-Lewis Acid Mediated Reaction

Abstract

A stereocontrolled synthesis of the (E)-alkene dipeptide isostere of Trp-Val is described. The stereospecific α-alkylation of the δ-amino-γ-mesyloxy-α, β-unsaturated ester via the organocyanocopper-Lewis acid mediated reaction, based on 1, 3-transfer of chirality, was successfully applied for the key step in the synthetic sequence.