Intramolecular Diels-Alder Reactions of Tethered Enoate Substituted Furans Induced by Dialkylaluminum Chloride.
Intramolecular Diels-Alder Reactions of Tethered Enoate Substituted Furans Induced by Dialkylaluminum Chloride.
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DOI：
10.1021/acs.joc.7b02117
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发表时间：
2017-11
期刊：
影响因子：
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通讯作者：
Sibylle Riedel;C. Maichle‐Mössmer;M. Maier
中科院分区：
文献类型：
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作者：
Sibylle Riedel;C. Maichle‐Mössmer;M. Maier
通过Sonogashira偶联获得的烯炔醇11和17的金（I）催化的环化异构化导致栓系的烯酸酯取代的呋喃14和19。虽然尝试热和几种刘易斯酸诱导的分子内Diels-Alder反应仍然没有结果，但二烷基氯化铝导致形成六氢茚和八氢萘衍生物20-23。它们的形成可以通过刘易斯酸诱导的环氧桥的开放与一个烷基转移到中间体环加合物来解释。
Gold(I)-catalyzed cycloisomerization of enynols 11 and 17, obtained by Sonogashira coupling, led to the tethered enoate-substituted furans 14 and 19. While attempts at thermal and several Lewis acid induced intramolecular Diels-Alder reactions remained fruitless, dialkylaluminum chloride led to the formation of hexahydroindene and octahydronaphthalene derivatives 20-23. Their formation can be explained by Lewis acid induced opening of the epoxy bridge with transfer of one alkyl group to the intermediate cycloadduct.