Tungstate-catalyzed oxidation of secondary amines to nitrones.. alpha.-Substitution of secondary amines via nitrones

S Murahashi, H Mitsui, T Shiota, T Tsuda…

Index: Murahashi, Shun-Ichi; Mitsui, Hitoshi; Shiota, Tatsuki; Tsuda, Tomoyasu; Watanabe, Shoji Journal of Organic Chemistry, 1990 , vol. 55, # 6 p. 1736 - 1744

Full Text: HTML

Citation Number: 283

Abstract

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 excellent 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 a-position of secondary amines can be ...