Electronic control of stereoselectivity in the metal hydride reductions of a series of substituted 3,4-dihydro-1,4-ethanonaphthalen-2(1H)-ones.
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概要
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The anti/syn stereoselectivity in the metal hydride reductions of a series of substituted 3,4-dihydro-1,4-ethanonaphthalen-2(1<I>H</I>)-ones was studied. The observed steroselectivity sequence was found to be parallel with the homoconjugation sequence except for the case of 5,8-dimethoxy-substituted derivative: the portion of anti attack increases as the benzene ring becomes electron-rich. The results were rationalized by Cieplak's transition state model or by the nonclassical carboncation model. A special coordinated transition state was considered to explain the results for 5,8-dimethoxy-substituted compound.
- 公益社団法人 日本化学会の論文
著者
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Oda Masaji
Department Of Chemistry Faculty Of Science Osaka University
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Okada Keiji
Department Of Chemistry Faculty Of Science Osaka University
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Tomita Seiji
Department of Chemistry, Faculty of Science, Osaka University
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