160865-32-7Relevant articles and documents
Direct chemical method for preparing 2,3-epoxyamides using sodium chlorite
Fuentes, Lilia,Osorio, Urbano,Quintero, Leticia,Hopfl, Herbert,Vazquez-Cabrera, Nixache,Sartillo-Piscil, Fernando
experimental part, p. 5515 - 5524 (2012/08/28)
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.
?-Allyl palladium methodology for selective deprotection of allylamines. Practical synthesis of secondary amines
Lemarie-Audoire, Sandrine,Savignac, Monique,Dupuis, Christophe,Genet, Jean Pierre
, p. 1157 - 1166 (2007/10/03)
The palladium-promoted deallylation of allylamines derived from primary and secondary amines is achieved with high to quantitative yield in the presence of 2-mercaptobenzoic acid as an allyl scavenger.This method was used for the sequential cleavage of diallylamines.A synthetic application of this procedure is presented in the preparation of secondary amines from diallylamines. - Keywords: allylamine; deallylation; sequential deprotection; ?-allyl palladium complexes; 2-mercaptobenzoic acid; substitution of amines
