Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes

The combination of electrolysis and the FeIII(PA)3/O2/CH3CN system was investigated for allylic hydroxylation of octahydronaphthalene derivatives. Substrates with a bridgehead double bond gave the allylic alcohol with α-preference, while non-bridgehead olefin did not react smoothly. This system is a useful tool for α-selective allylic hydroxylation of octahydronaphthalene derivatives with a bridgehead double bond as model compounds for the AB fused ring of cholesterols.