Nickel-Catalyzed Regio- and Enantioselective Ring Opening of 3,4-Epoxy Amides and Esters with Aromatic Amines

Herein we present a nickel-catalyzed regio- and enantioselective ring opening reaction of 3,4-epoxy amides and esters with aromatic amines as nucleophiles. This method features high regiocontrol, diastereospecific S(N)2 reaction pathway, broad substrate scope, and mild reaction conditions, furnishing a wide range of gamma-amino acid derivatives in a highly enantioselective manner. Notably, the selective nucleophilic attack to the C-4 position of epoxides is controlled by the directing effect of the pendant carbonyl group.

Automated summary

Here, we report a nickel-catalyzed regio- and enantioselective ring opening reaction of 3,4-epoxy amides and esters with aromatic amines as nucleophiles. This method demonstrates high regiocontrol, diastereospecific S(N)2 reaction pathway, broad substrate scope, and mild reaction conditions, enabling the synthesis of a wide range of gamma-amino acid derivatives in a highly enantioselective manner. Notably, the selective nucleophilic attack to the C-4 position of epoxides is controlled by the directing effect of the pendant carbonyl group.