Allylic Amination and 1,2‐Diamination with a Modified Diimidoselenium Reagent

Replacing the tosyl with a nosyl (Ns) group—that is the key to an improved method for both allylic amination of olefins and 1,2-diamination of 1,3-dienes. The protecting group recently introduced by Fukuyama et al., the 0-nitrobenzenesulfonyl (nosyl) group, can be employed with diimidoselenium reagents. The resulting nosyl-amides can be converted into primary and secondary amines in good to excellent yields. An example of this approach is sketched below in reaction (a) (R  Me, CH2CHCH2, CH2Ph).