Oxidative N-Heterocyclic Carbene Catalyzed Dearomatization of Indoles to Spirocyclic Indolenines with a Quaternary Carbon Stereocenter
Oxidative N-Heterocyclic Carbene Catalyzed Dearomatization of Indoles to Spirocyclic Indolenines with a Quaternary Carbon Stereocenter
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DOI：
10.1002/anie.201701485
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发表时间：
2017-06-19
影响因子：
16.6
通讯作者：
Studer, Armido
中科院分区：
文献类型：
--
作者：
Bera, Srikrishna;Daniliuc, Constantin G.;Studer, Armido
证明了一种利用氧化 N-杂环卡宾催化对吲哚进行不对称分子内脱芳构化的有效方法。以优异的产率和优异的对映选择性获得了具有全碳四元立构中心的有价值的光学活性螺环假吲哚。起始吲哚很容易制备，反应通过原位生成的酰基唑鎓中间体进行分子内吲哚 3-酰化反应，形成螺环酮部分。
An efficient method for the asymmetric intramolecular dearomatization of indoles by using oxidative N-heterocyclic carbene catalysis is demonstrated. Valuable optically active spirocyclic indolenines bearing an all-carbon quaternary stereocenter are obtained in excellent yields and with excellent enantioselectivity. The starting indoles are readily prepared and the reactions proceed through an intramolecular indole 3-acylation with an in situ generated acyl azolium intermediate to form a spirocyclic ketone moiety.