Yttrium-Catalyzed Regioselective Aminolysis of 2,3-Epoxy Esters and Amides

Abstract Herein, an yttrium-catalyzed regioselective ring-opening reaction of 2,3-epoxy esters and amides with amines as nucleophiles is presented. This method features high regiocontrol, an enantiospecific SN2 reaction pathway, a broad substrate scope, and mild reaction conditions, furnishing a wide range of α-hydroxy β-amino esters and amides in regioisomerically pure forms. Notably, the selective nucleophilic attack to the C-3 position is controlled by the directing effect of the carbonyl group of the substrates.