Journal
ORGANIC LETTERS
Volume 19, Issue 17, Pages 4508-4511Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02068
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Funding
- NSFC [21372217, 21572223, 21572224, 21602217]
- Sichuan Youth Science and Technology Foundation [2015JQ0041, 2016JQ0024]
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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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