600734-14-3Relevant articles and documents
Synthesis of Aromatic (E)- or (Z)-α,β-Unsaturated Amides with Total or Very High Selectivity from α,β-Epoxyamides and Samarium Diiodide
Concellon, Jose M.,Bardales, Eva
, p. 9492 - 9495 (2003)
Highly stereoselective synthesis of aromatic α,β-unsaturated amides was achieved by treatment of aromatic α,β-epoxyamides with samarium diiodide. The starting compounds 1 and 3 are easily prepared by the reaction of enolates derived from α-chloroamides wi
Unusual reductive cleavage of 3-aryl-2,3-epoxyamides by using samarium diiodide. Synthesis of 3-aryl-3-deuterio-2-hydroxyamides with total regioselectivity
Concellón, José M.,Bardales, Eva,Gómez, Cecilia
, p. 5323 - 5326 (2007/10/03)
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 α-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.
