Chiral Imidodiphosphoric Acids-Catalyzed Friedel-Crafts Reactions of Indoles/Pyrroles with 3-Hydroxy-indolyloxindoles: Enantioselective Synthesis of 3,3-Diaryloxindoles
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- 作者：Ming-Hua Zhuo ; Guo-Feng Liu ; Shan-Liang Song ; Dong An ; Jigang Gao ; Liangyu Zheng and Suoqin Zhang
- 关键词：enantioenriched 3 ; 3-diaryloxindoles ; Friedel&ndash ; Crafts reaction ; 3-hydroxy-3-indolyloxindoles ; indoles ; pyrroles
- 刊名：Advanced Synthesis & Catalysis
- 出版年：2016
- 出版时间：March 3, 2016
- 年：2016
- 卷：358
- 期：5
- 页码：808-815
- 全文大小：2292K
- ISSN：1615-4169
文摘
The first enantioselective Friedel–Crafts alkylation of indoles and pyrroles with 3-hydroxy-3-indolyloxindoles to access two novel types of 3,3-diaryloxindoles catalyzed by chiral imidodiphosphoric acids has been reported. A range of quaternary carbon centered 3,3-diaryloxindoles were synthesized in high yield (up to >99%) with excellent enantioselectivity (up to 98% ee) at low catalyst loadings (as low as 0.5 mol%). The Friedel–Crafts reaction between indoles and 3-hydroxy-3-indolyloxindoles is amenable to gram scale syntheses.