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. 2017 Sep 1;19(17):4508-4511.
doi: 10.1021/acs.orglett.7b02068. Epub 2017 Aug 15.

Multiple Hydrogen-Bonding Bifunctional Thiourea-Catalyzed Asymmetric Dearomative [4 + 2] Annulation of 3-Nitroindoles: Highly Enantioselective Access to Hydrocarbazole Skeletons

Deng-Feng Yue  1 , Jian-Qiang Zhao  2 , Xiao-Zhen Chen, Yan Zhou, Xiao-Mei Zhang, Xiao-Ying Xu, Wei-Cheng Yuan
Affiliations

Multiple Hydrogen-Bonding Bifunctional Thiourea-Catalyzed Asymmetric Dearomative [4 + 2] Annulation of 3-Nitroindoles: Highly Enantioselective Access to Hydrocarbazole Skeletons

Deng-Feng Yue et al. Org Lett. .

Abstract

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.

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