SN2′ Ring opening of aziridines bearing an α,β-unsaturated ester group with organocopper reagents. A new stereoselective synthetic route to (E)-alkene dipeptide isosteres

Regio- and stereo-selective synthesis of (E)-alkene dipeptide isosteres has been successfully achieved by exposing both (E)- and (Z)-N-(4-methylphenyl)sulfonyl-γ,δ-epimino-α,β-enoates to organocopper reagents at –78 °C for 30 min.