Carbocyclic ring formation by the intramolecular reaction between enol silyl ether and allylic acetate moieties.
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概要
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The title reaction of <I>trans</I>-3-acetoxy-4-(4-methyl-3-trimethylsiloxy-3-pentenyl)cyclohexene proceeds in the presence of Et<SUB>2</SUB>AlOAr, where Ar=2,6-di-<I>t</I>-butyl-4-methylphenyl, affording stereospecifically the <I>cis</I> isomer of 2,2-dimethylbicyclo[4.4.0]dec-9-en-3-one. In contrast, the <I>cis</I>-disubstituted cyclohexene compound reacts only sluggishly to produce a mixture of the <I>cis</I>- and <I>trans</I>-fused octalones. Similar stereospecific effect of the allylic double bond configuration on the ease of cyclization has been observed in the synthesis of karahanaenone from 3,7-dimethyl-6-trimethylsiloxy-2,6-octadienyl acetate and related reactions.
- 公益社団法人 日本化学会の論文
著者
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Oshima Koichiro
Department Of Industrial Chemistry Faculty Of Engineering Kyoto University
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Yamamoto Hisashi
Department Applied Chemistry Nagoya University
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Nozaki Hitosi
Department of Industrial Chemistry, Faculty of Engineering Kyoto University
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Itoh Akira
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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Itoh Akira
Department of Industrial Chemistry, Faculty of Engineering, Kyoto University
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