Selective allylic hydroxylation of octahydronaphthalene derivatives with a bridgehead double bond using electrochemical method with iron picolinate complexes.
The combination of electrolysis and the Fe(III)(PA)3/O2/CH3CN system was investigated for allylic hydroxylation of octahydronaphthalene derivatives. Substrates with a bridgehead double bond gave the allylic alcohol with alpha-preference, while non-bridgehead olefin did not react smoothly. This system is a useful tool for alpha-selective allylic hydroxylation of octahydronaphthalene derivatives with a bridgehead double bond as model compounds for the AB fused ring of cholesterols.
Okamoto
Iwao
I
Showa Pharmaceutical University, Machida, Tokyo, Japan.
Funaki
Wataru
W
Nobuchika
Sachiyo
S
Sawamura
Mika
M
Kotani
Eiichi
E
Takeya
Tetsuya
T
D002784:Cholesterol / Q000737:chemistry; D004563:Electrochemistry; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry*; D010084:Oxidation-Reduction; D010848:Picolinic Acids / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
D009281:Naphthalenes; D010848:Picolinic Acids; D002784:Cholesterol; C030614:picolinic acid