Concellón José M, Bardales Eva
Departamento de Química Orgánica e Inorgánica, Facultad de Química Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain.
Org Lett. 2003 Dec 11;5(25):4783-5. doi: 10.1021/ol035757k.
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]
描述了一种通过二碘化钐和甲醇促进的脂肪族α,β-环氧酰胺的C(β)-O键还原裂解，以完全区域选择性合成脂肪族α-羟基酰胺的通用方法。对映体纯的脂肪族α,β-环氧酰胺的处理得到了对映体富集的脂肪族α-羟基酰胺。已提出一种自由基机理来解释该反应。[反应：见正文]
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