Unusual reductive cleavage of 3-aryl-2,3-epoxyamides by using samarium diiodide. Synthesis of 3-aryl-3-deuterio-2-hydroxyamides with total regioselectivity

摘要

Ring-opening of 3-aryl-2,3-epoxyamides 1 was achieved by using samarium diiodide and D_2O, yielding 3-aryl-3-deuterio-2-hydroxyamides 2 with total regioselectivity. The starting compounds 1 were easily prepared by reaction of the corresponding lithium or potassium enolates of α-chloroamides with aldehydes or ketones. When the reaction was carried out in the presence of H_2O instead of D_2O, the corresponding 3-aryl*2-hydroxyamides were isolated. The treatment of enantiopure 3-aryl-2,3-epoxyamides afforded optically active 3-aryl-2-hydroxyamides.