Construction of the Benzomesembrine Skeleton: Palladium(0)-Catalyzed Intermolecular Arylative Dearomatization of alpha-Naphthols and Subsequent Aza-Michael Reaction

Construction of the Benzomesembrine Skeleton: Palladium(0)-Catalyzed Intermolecular Arylative Dearomatization of alpha-Naphthols and Subsequent Aza-Michael Reaction
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Benzomesembrine 骨架的构建:钯 (0) 催化的 α-萘酚分子间芳基化脱芳构化和随后的 Aza-Michael 反应

DOI:
10.1002/anie.201703674
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发表时间:
2017
期刊:
Angewandte Chemie International Edition
影响因子:
--
通讯作者:
You Shu-Li
You Shu-Li
中科院分区:
其他
文献类型:
--
作者:
Xu Ren-Qi;Gu Qing;You Shu-Li

文献摘要

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描述了一种新型钯 (0) 催化的 α-萘酚分子间芳基化脱芳构化反应以及随后的氮杂迈克尔反应。通过连续的芳基化脱芳构化和迈克尔加成反应,有效构建了两个相邻的立体中心。通过利用该方法,合成了结构多样的苯并菊叶衍生物,具有优异的产率和化学选择性。苯甲菊碱产品被证明可以进行多种官能团转化。
A novel palladium(0)‐catalyzed intermolecular arylative dearomatization of α‐naphthols and subsequent aza‐Michael reaction is described. Two adjacent stereocenters were constructed efficiently through consecutive arylative dearomatization and Michael addition reactions. By utilizing this method, structurally diverse benzomesembrine derivatives were synthesized with excellent yields and chemoselectivity. The benzomesembrine products were shown to undergo versatile functional‐group transformations.