Palladium-catalyzed cascade one-pot synthesis of 5-arylmethylisoxazolidines from N-homoallylhydroxylamines with aryl bromides

A novel method for the synthesis of 5-arylmethylisoxazolidines via palladium-catalyzed reactions of aryl bromides with N-homoallylhydroxylamines is described. This reaction effects intramolecular C-O bond formation with concomitant intermolecular formation of a C-C bond in moderate to good yields. Moderate to excellent diastereoselectivities are observed for the formation of the isoxazolidines. The catalytic system has a tolerance to a wide variety of functional groups.