The use of samarium or sodium iodide salts as an alternative for the aza-Henry reaction

A novel reaction of bromonitromethane with a variety of imines in very mild conditions promoted by SmI2 and NaI to afford nitroamines or bromonitroamines is described. When these reactions were performed on sugar-based imines, the corresponding nitroamines or bromonitroamines were obtained in high yields and from moderate to good stereoselectivities. Synthetic possibilities of nitroamines were also shown by their reduction with SmI2/H2O in the presence of pyrrolidine at room temperature. A mechanism is proposed for this novel aza-Henry reaction.