Base-promoted Acyloin Rearrangement of 1,8-Di-tert-butyldimethylsilyloxybicyclo[2.2.2]oct-5-en-2-ones

Sadamu Katayama; Masashige Yamauchi

doi:10.1248/cpb.53.666

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Base-promoted Acyloin Rearrangement of 1,8-Di-tert-butyldimethylsilyloxybicyclo[2.2.2]oct-5-en-2-ones

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Keywords: 18-crown-6, bicyclo[3.2.1]oct-3-en-2-one, bicyclo[2.2.2]oct-5-en-2-one, potassium hydride, potassium bistrimethylsilylamide, base-promoted acyloin rearrangement

JOURNAL FREE ACCESS

2005 Volume 53 Issue 6 Pages 666-670

DOI https://doi.org/10.1248/cpb.53.666

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Abstract

Treatment of 1,8-di-tert-butyldimethylsilyloxybicyclo[2.2.2]oct-5-en-2-ones having an electron-withdrawing group such as a nitro, formyl, cyano, and imido group at C-7 with a strong base (potassium hydride, or potassium bistrimethylsilylamide, etc.), resulted in an acyloin rearrangement reaction accompanied by retention of two silyloxy groups to afford 1,8-disilyloxybicyclo[3.2.1]oct-3-en-2-ones.

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