A New Electrochemical System for Stereoselective Allylic Hydroxylation of Cholesteryl Acetate with Dioxygen Induced by Iron Picolinate Complexes

Iwao Okamoto; Wataru Funaki; Kyosuke Nakaya; Eiichi Kotani; Tetsuya Takeya

doi:10.1248/cpb.52.756

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A New Electrochemical System for Stereoselective Allylic Hydroxylation of Cholesteryl Acetate with Dioxygen Induced by Iron Picolinate Complexes

Iwao Okamoto, Wataru Funaki, Kyosuke Nakaya, Eiichi Kotani, Tetsuya Takeya

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

JOURNAL FREE ACCESS

2004 Volume 52 Issue 6 Pages 756-759

DOI https://doi.org/10.1248/cpb.52.756

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Abstract

The oxygenation reaction of cholesteryl acetate 1 was examined with the Fe^III(PA)₃/O₂/MeCN system using an electrochemical method. The constant potential technique gave mainly the 7-hydroxylated product stereoselectively, along with the 7-oxo product. This oxygenation system is mechanistically unique, requiring iron catalyst, dioxygen, and both cathode and anode.

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