Copper-catalyzed intermolecular oxyamination of olefins using carboxylic acids and O-benzoylhydroxylamines

• Brett N. Hemric and
• Qiu Wang

Beilstein J. Org. Chem. 2016, 12, 22–28, doi:10.3762/bjoc.12.4

• . Keywords: copper; electrophilic amination; olefin oxyamination; Introduction The 1,2-oxyamino motif is highly valuable and found in a vast range of biologically active natural products, pharmaceuticals, and agrochemicals (Figure 1) [1][2]. Representative examples include salmeterol (Advair®), a β2

• class of molecules is highly valued. Toward this end, intermolecular olefin oxyamination allows for direct and modular installation of both oxygen and amino groups to readily available olefins in a single step, representing a powerful and appealing approach over multistep sequences [7][8][9]. Sharpless

• reported the first examples of this strategy using osmium tetroxide and amines to generate imido osmium intermediates (Scheme 1A) [10][11][12]. Although this transformation has received extensive application, the development of less toxic olefin oxyamination methods is greatly desired. In 2006, Stahl and