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 γ-lactols has been developed. The present reaction proceeds through a sequence of radical processes involving oxynitration followed by aerobic oxidation of an sp3 C–H bond. This multifunctionalization reaction requires neither metallic reagents nor photolysis and proceeds under mild conditions.
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