Base-promoted acyloin rearrangement of 1,8-di-tert-butyldimethylsilyloxybicyclo[2.2.2]oct-5-en-2-ones.
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.
Katayama
Sadamu
S
Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-02, Japan. skataya@josai.ac.jp
Yamauchi
Masashige
M
D004583:Electrons; D005233:Fatty Alcohols / Q000032:analysis / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D017680:Potassium Compounds / Q000032:analysis / Q000737:chemistry
D005233:Fatty Alcohols; D017680:Potassium Compounds; C011159:acyloin