ol8022165_si_003.cif (17.37 kB)

Metal-Free Oxidative Cyclization of Urea-Tethered Alkenes with Hypervalent Iodine

Download (17.37 kB)
dataset
posted on 06.11.2008 by Brian M. Cochran, Forrest E. Michael
A metal-free oxidative cyclization of ureas onto unactivated alkenes using iodosylbenzene and an acid promoter is described. The products isolated are predominantly bicyclic isoureas resulting from an intramolecular oxyamination reaction. The acid type and urea substitution have a strong effect on the product formed. A variety of substrates form the isourea with high diastereoselectivity via syn addition including di- and trisubstituted alkenes. Hydrolysis of the isourea gives access to new diastereomerically pure prolinol derivatives.

History

Exports