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Direct Chemical Method for Preparing 2,3-Epoxyamides Using Sodium Chlorite

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posted on 06.07.2012, 00:00 by Lilia Fuentes, Urbano Osorio, Leticia Quintero, Herbert Höpfl, Nixache Vázquez-Cabrera, Fernando Sartillo-Piscil
A direct method for preparing 2,3-epoxyamides from tertiary allylamines via a tandem C–H oxidation/double bond epoxidation using sodium chlorite is reported. Apparently, the reaction course consists of two steps: (i) allylic oxidation of the starting allylamine to corresponding unsaturated allylamide with sodium chlorite followed by (ii) epoxidation of the allylamide to the 2,3-epoxyamide mediated by hypochlorite ion, which is formed in situ by reduction of sodium chlorite. The reaction conditions tolerate the presence of free hydroxyl groups and typical functional groups such as TBS, aryl, alkyl, allyl, acetyl, and benzyl groups; however, when an activated aromatic ring (e.g., sesamol) is present in the substrate, the use of a scavenger is necessary.