Catalyst-Controlled Amino- versus Oxy-Acetoxylation of Urea-Tethered Alkenes: Efficient Synthesis of Cyclic Ureas and Isoureas

A catalyst-controlled vicinal amino- versus oxy-acetoxylation of alkenes with PhI(OAc)(2) as the oxidant is described. The divergent synthesis of cyclic ureas and isoureas was achieved in good yields under mild conditions employing ambident urea nucleophiles. Both terminal and internal alkenes are compatible with this reaction protocol.