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

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 &...

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Veröffentlicht in:Organic letters 2017-09, Vol.19 (17), p.4508-4511
Hauptverfasser: Yue, Deng-Feng, Zhao, Jian-Qiang, Chen, Xiao-Zhen, Zhou, Yan, Zhang, Xiao-Mei, Xu, Xiao-Ying, Yuan, Wei-Cheng
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container_end_page 4511
container_issue 17
container_start_page 4508
container_title Organic letters
container_volume 19
creator Yue, Deng-Feng
Zhao, Jian-Qiang
Chen, Xiao-Zhen
Zhou, Yan
Zhang, Xiao-Mei
Xu, Xiao-Ying
Yuan, Wei-Cheng
description 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.
doi_str_mv 10.1021/acs.orglett.7b02068
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title Multiple Hydrogen-Bonding Bifunctional Thiourea-Catalyzed Asymmetric Dearomative [4 + 2] Annulation of 3‑Nitroindoles: Highly Enantioselective Access to Hydrocarbazole Skeletons
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