Direct chemical method for preparing 2,3-epoxyamides using sodium chlorite.
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.
Centro de Investigación de la Facultad de Ciencias Químicas, BUAP, 14 Sur Esq. San Claudio, San Manuel, 72570, Puebla, México.
Lilia
L
Fuentes
Urbano
U
Osorio
Leticia
L
Quintero
Herbert
H
Höpfl
Nixache
N
Vázquez-Cabrera
Fernando
F
Sartillo-Piscil
D000499:Allylamine / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D002712:Chlorides; D004852:Epoxy Compounds; D000499:Allylamine; C001599:chlorite