Synthesis of High Enantiopurity N-Protected α-Amino Ketones by Thiol Ester-Organostannane Cross-Coupling using pH-Neutral Conditions

摘要

An efficient synthesis of high enantiopurity N-protected α-amino ketones is described. Complementing other studies using boronic acids and thiol esters, this Cu(I) diphenylphosphinate (CuDPP)-mediated, palladium-catalyzed coupling of α-amino thiol esters with aryl, heteroaryl, allyl and alkenyl organostannanes gives N-protected α-amino ketones in high yields with high enantiopurity (in almost all cases) under mild and pH-neutral reaction conditions. The viability of π-deficient heteroarylstannanes is an advantage of this reaction compared to the related boronic acid system.