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 |
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container_title | Organic letters |
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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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Lett</addtitle><date>2017-09-01</date><risdate>2017</risdate><volume>19</volume><issue>17</issue><spage>4508</spage><epage>4511</epage><pages>4508-4511</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><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><cop>United States</cop><pub>American Chemical Society</pub><pmid>28809570</pmid><doi>10.1021/acs.orglett.7b02068</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-4850-8981</orcidid></addata></record> |
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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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