Preparation of a cycloheptane ring from a 1,2-diketone with high stereoselectivity.
Treatment of 1,6-dialkylhexa-1,5-diene-3,4-diones with bis(iodozincio)methane gave zinc alkoxides of cis-5,6-dialkylcyclohepta-3,7-diene-1,3-diol in good yields at room temperature. The reaction proceeded with high stereospecificity. Bis(iodozincio)methane converted the diketone into the cis-divinylcyclopropane-1,2-diol stereoselectively; this diol transformed into the corresponding cycloheptane derivative stereospecifically via Cope rearrangement.
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai-Katsura, Nishikyo, Kyoto 615-8510, Japan.
Yoshiaki
Y
Takada
Kenichi
K
Nomura
Seijiro
S
Matsubara