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

Authors :
Deng-Feng Yue
Jian-Qiang Zhao
Xiao-Zhen Chen
Yan Zhou
Xiao-Mei Zhang
Xiao-Ying Xu
Wei-Cheng Yuan
Source :
Organic Letters. Sep2017, Vol. 19 Issue 17, p4508-4511. 4p.
Publication Year :
2017

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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
15237060
Volume :
19
Issue :
17
Database :
Academic Search Index
Journal :
Organic Letters
Publication Type :
Academic Journal
Accession number :
124966641
Full Text :
https://doi.org/10.1021/acs.orglett.7b02068