分子内力
区域选择性
化学
杂原子
取代基
吲哚试验
戒指(化学)
催化作用
质子化
立体化学
苯乙烯
药物化学
有机化学
共聚物
离子
聚合物
作者
Xiao Cai,Anargul Tohti,Cristián Ramírez,Hassan Harb,James C. Fettinger,Hrant P. Hratchian,Benjamin J. Stokes
出处
期刊:Organic Letters
[American Chemical Society]
日期:2019-02-26
卷期号:21 (6): 1574-1577
被引量:9
标识
DOI:10.1021/acs.orglett.9b00043
摘要
Readily prepared cis-β-(α′,α′-dimethyl)-4′-methindolylstyrenes undergo acid-catalyzed intramolecular hydroindolation to afford tetrahydrobenzo[cd]indoles. Our experimental and computational investigations suggest that dispersive interactions between the indole and styrene preorganize substrates such that 6-membered ring formation is preferred, apparently via concerted protonation and C–C bond formation. When dispersion is attenuated (by a substituent or heteroatom), regioselectivity erodes and competing oligomerization predominates for cis substrates. Similarly, all trans-configured substrates that we evaluated failed to cyclize efficiently.
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