An iron-catalyzed diastereoselective intermolecular olefin amino-oxygenation reaction is reported, which proceeds via an iron-nitrenoid generated by the N− O bond cleavage of a functionalized hydroxylamine. In this reaction, a bench-stable hydroxylamine derivative is used as the amination reagent and oxidant. This method tolerates a range of synthetically valuable substrates that have been all incompatible with existing amino-oxygenation methods. It can also provide amino alcohol derivatives with regio- and stereochemical arrays complementary to known amino-oxygenation methods.
Lu, D.-F., Zhu, C.-L., Jia, Z.-X., & Xu, H. (2014). Iron(II)-Catalyzed Intermolecular Amino-Oxygenation of Olefins through the N–O Bond Cleavage of Functionalized Hydroxylamines. Journal of the American Chemical Society, 136(38), 13186-13189. doi:10.1021/ja508057u