Multifunctionalization of alkenes via aerobic oxynitration and sp3 C-H oxidation.

A method for direct functionalization of three positions including an unactivated C-H bond of aliphatic alkenes using tert-butyl nitrite and molecular oxygen to give gamma-lactols has been developed. The present reaction proceeds through a sequence of radical processes involving oxynitration followed by aerobic oxidation of an sp(3) C-H bond. This multifunctionalization reaction requires neither metallic reagents nor photolysis and proceeds under mild conditions.