Iodolactamization of γ,δ-unsaturated oxazolines

The iodolactamization of a series of γ,δ-unsaturated oxazolines has been studied (i → iii). The data presented establish that the resulting hydroxy iodo lactams are produced in high yield and regioselectively. No asymmetric induction is observed with substituents on the oxazoline ring or at the homoallylic position; however, moderate to high 1,2-asymmetric induction can be obtained with a substituent at the allylic position. Most importantly, these results establish that the iodolactamization of γ,δ-unsaturated oxazolines is a kinetically controlled process proceeding via the intermediacy of ii.