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

Iwao Okamoto; Wataru Funaki; Sachiyo Nobuchika; Mika Sawamura; Eiichi Kotani; Tetsuya Takeya

doi:10.1248/cpb.53.248

Notes

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

Iwao Okamoto, Wataru Funaki, Sachiyo Nobuchika, Mika Sawamura, Eiichi Kotani, Tetsuya Takeya

Author information

Keywords: allylic hydroxylation, iron catalysis, electrochemical oxidation, 7α-hydroxylation

JOURNAL FREE ACCESS

2005 Volume 53 Issue 2 Pages 248-252

DOI https://doi.org/10.1248/cpb.53.248

Details

Abstract

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 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.

Corresponding author

Register with J-STAGE for free!