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. 2003 Dec 11;5(25):4783-5.
doi: 10.1021/ol035757k.

The first transformation of aliphatic alpha,beta-epoxyamides into alpha-hydroxyamides

José M Concellón  1 , Eva Bardales
Affiliations

The first transformation of aliphatic alpha,beta-epoxyamides into alpha-hydroxyamides

José M Concellón et al. Org Lett. .

Abstract

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]

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