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

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 S(N)2 reaction pathway, a broad substrate scope, and mild reaction conditions, furnishing a wide range of alpha-hydroxy beta-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.

Automated summary

Here, the authors present a yttrium-catalyzed regioselective ring-opening reaction between 2,3-epoxy esters and amides with amines as nucleophiles. This method offers high regiocontrol, an enantiospecific S(N)2 reaction pathway, a wide substrate scope, and mild reaction conditions, resulting in the synthesis of a broad range of regioisomerically pure alpha-hydroxy beta-amino esters and amides. Importantly, the selective nucleophilic attack at the C-3 position is controlled by the directing effect of the carbonyl group of the substrates.