Copper-catalyzed intermolecular asymmetric propargylic dearomatization of indoles.

Autor: Shao W; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn., Li H; Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Physics and Chemistry Detecting Centre, Xinjiang University, Urumqi 830046 (China)., Liu C; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn., Liu CJ; Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Physics and Chemistry Detecting Centre, Xinjiang University, Urumqi 830046 (China)., You SL; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn. slyou@sioc.ac.cn.; Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin 300072 (China). slyou@sioc.ac.cn.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2015 Jun 22; Vol. 54 (26), pp. 7684-7. Date of Electronic Publication: 2015 May 12.
DOI: 10.1002/anie.201503042
Abstrakt: The first copper-catalyzed intermolecular dearomatization of indoles by an asymmetric propargylic substitution reaction was developed. This method provides a highly efficient synthesis of versatile furoindoline and pyrroloindoline derivatives containing a quaternary carbon stereogenic center and a terminal alkyne moiety with up to 86 % yield and 98 % ee.
(© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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