Preparation of a cycloheptane ring from a 1,2-diketone with high stereoselectivity |
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Authors: | Takada Yoshiaki Nomura Kenichi Matsubara Seijiro |
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Institution: | Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai-Katsura, Nishikyo, Kyoto 615-8510, Japan. |
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Abstract: | 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. |
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