Multiple Hydrogen-Bonding Bifunctional Thiourea-Catalyzed Asymmetric Dearomative [4 2] Annulation of 3-Nitroindoles: Highly Enantioselective Access to Hydrocarbazole Skeletons
Multiple Hydrogen-Bonding Bifunctional Thiourea-Catalyzed Asymmetric Dearomative [4 2] Annulation of 3-Nitroindoles: Highly Enantioselective Access to Hydrocarbazole Skeletons
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多重氢键双功能硫脲催化的不对称脱芳香剂 [4 2] 3-硝基吲哚的环化：高度对映选择性获得氢咔唑骨架
DOI：
10.1021/acs.orglett.7b02068
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发表时间：
2017
期刊：
影响因子：
5.2
通讯作者：
Yuan Wei Cheng
中科院分区：
文献类型：
--
作者：
Yue Deng Feng;Zhao Jian Riang;Chen Xiao Zhen;Zhou Yan;Zhang Xiao Mei;Xu Xiao Ying;Yuan Wei Cheng
报道了一种利用Nazarov试剂对3-硝基吲哚进行[4 + 2]环化反应，对映选择性地构筑氢化咔唑骨架的方法。该反应使用多氢键双官能硫脲作为催化剂，并且具有高度的非对映选择性和对映选择性（高达>20：1 dr和> 99%ee）。该方案被证明是由间接规模的实验和产品的通用转换。催化剂中的多重氢键对反应活性和立体选择性起着关键作用。
A method for the enantioselective construction of hydrocarbazole skeletons through dearomative [4 + 2] annulation of 3-nitroindoles with Nazarov reagents is reported. The reactions use multiple hydrogen-bonding bifunctional thiourea as catalyst and are highly diastereo- and enantioselective (up to >20:1 dr and >99% ee). The protocol was demonstrated by preparative-scale experiment and the versatile conversion of the products. The multiple hydrogen-bonding in the catalyst plays a pivotal role in the reactivity and stereoselectivity.