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

Ring-opening of 3-aryl-2,3-epoxyamides 1 was achieved by using samarium diiodide and D2O, 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 alpha-chloroamides with aldehydes or ketones. When the reaction was carried out in the presence of H2O instead of D2O, the corresponding 3-aryl-2-hydroxyamides were isolated. The treatment of enantiopure 3-aryl-2,3-epoxyamides afforded optically active 3-aryl-2-hydroxyamides. (C) 2003 Elsevier Science Ltd. All rights reserved.