Tungstate-Catalyzed Oxidation of Secondary Amines to Nitrones. α-Substitution of Secondary Amines via Nitrones

Article abstract of DOI:10.1021/jo00293a013

The sodium tungstate catalyzed oxidation of secondary amines with hydrogen peroxide gives the corresponding nitrones.Acyclic and cyclic nitrones can be obtained from secondary amines in a single step in good to escellent yields.The oxidation of secondary amines in the presence of alkenes gives isoxazolidines by 1,3-dipolar cycloaddition of nitrones.Introduction of a substituent at the α-position of secondary amines can be performed upon oxidation of secondary amines and subsequent treatment with various nucleophiles.