环加成
化学
双功能
金鸡纳
角鲨胺
醌
对映选择合成
组合化学
有机催化
催化作用
有机化学
作者
Shun Zhou,Hui-Ling Qian,Jian‐Qiang Zhao,Yong You,Zhenhua Wang,Jin-Qing Yin,Yanping Zhang,Mingfeng Chen,Wei‐Cheng Yuan
摘要
A formal [4 + 2] cycloaddition of 3-nitroindoles with ortho-aminophenyl p-quinone methides via a dearomatization process was developed. This method provides a facile approach for preparing tetrahydro-5H-indolo[2,3-b]quinolones with good results. With the bifunctional Cinchona alkaloid-squaramide as the catalyst, the asymmetric version of the reaction successfully afforded the corresponding chiral products with moderate to good enantioselectivities. This work represents the first dearomative cycloaddition of electron-deficient heteroarenes triggered by aza-Michael addition from p-QMs.
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