Stereocontrolled Synthesis Of Alpha-Amino-Alpha '-Alkoxy Ketones By A Copper-Catalyzed Cross-Coupling Of Peptidic Thiol Esters And Alpha-Alkoxyalkylstannanes

A stereocontrolled synthesis of alpha-amino-alpha'-alkoxy ketones is described. This pH-neutral copper(I) thlophene-2-carboxylate (CuTC)-catalyzed cross-coupling of amino acid thiol esters and chiral nonracemic alpha-alkoxyalkylstannanes gives alpha-amino-alpha'-alkoxy ketones in good to excellent yields with complete retention of configuration at the alpha-amino- and alpha-alkoxy-substituted stereocenters.