Stereoselectivity of Diels-Alder reactions of 6,7-dioxabicyclo(3.2.2)-nona-3,8-dien-2-one and 6,7-diethoxycarbonyl-6,7-diazabicyclo(3.2.2)nona-3,8-dien-2-one.
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概要
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A Diels–Alder reaction of 6,7-dioxabicyclo[3.2.2]nona-3,8-dien-2-one (<B>2</B>) with cyclopentadiene gave the <I>cis</I>-<I>endo</I>-[4+2] adduct and the <I>trans</I>-<I>endo</I>-[4+2] adduct. Their yields were improved when the reaction was carried out under high-pressure conditions. The reaction of 6,7-diethoxycarbonyl-6,7-diazabicyclo[3.2.2]nona-3,8-dien-2-one (<B>3</B>) gave the <I>cis</I>-<I>endo</I>-[4+2] adduct. Reactions of <B>2</B> and <B>3</B> with isobenzofuran and its 1,3-diphenyl derivative gave the thermodynamically-controlled <I>exo</I>-[4+2] adducts.
- 公益社団法人 日本化学会の論文
著者
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Mori Akira
Research Department Of Mechanical Control Research Center Research Division Komatsu Ltd.
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Tsuda Tohru
Graduate School of Engineering Sciences, 39, Kyushu University
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Sugiyama Shigeru
Research Institute of Industrial Science, 86, Kyushu University
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Takeshita Hitoshi
Research Institute of Industrial Sciece, 86, Kyushu University
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