The first transformation of aliphatic alpha,beta-epoxyamides into alpha-hydroxyamides.
A general synthesis of aliphatic alpha-hydroxyamides with total regioselectivity by a reductive cleaveage of the C(beta)-O bond of aliphatic alpha,beta-epoxyamides, promoted by samarium diiodide and MeOH, is described. The treatment of enantiopure aliphatic alpha,beta-epoxyamides afforded enantiomerically enriched aliphatic alpha-hydroxyamides. A radical mechanism has been proposed to explain this reaction. [reaction: see text]
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain.
Bardales
Eva
E
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure; D012493:Samarium / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D004852:Epoxy Compounds; D007454:Iodides; D012493:Samarium; C409809:samarium diiodide