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Short Paper | Special issue | Vol 93, No. 2, 2016, pp.833-844
Published online, 20th January, 2016
DOI: 10.3987/COM-15-S(T)65
Magnesium-Alkoxide Directed Photoaddition of Tetrahydrofurans to γ,γ-Disubstituted Allylic Alcohols

Yasutaka Watanabe, Takahiro Sakai, Hajime Maeda, Masahito Segi, Takahiro Soeta, and Yutaka Ukaji*

*Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

Magnesium-alkoxide directed photoaddition of tetrahydrofurans to γ,γ-disubstituted allylic alcohols was achieved. When the allylic alcohols were treated with Grignard reagent in THF under light, the corresponding γ-(2-tetrahydrofuryl) substituted alcohols were regioselectively obtained in up to 82% yield. The conversion of the hydroxyl group to the corresponding bromomagnesium alkoxide was crucial.