| Chiral Bronsted Acid Directed Iron-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with β-Aryl α'-Hydroxy Enones | |
| Department | 羰基合成与选择氧化国家重点实验室 |
Yang L(杨磊) ; Zhu QM(朱其明); Guo SM(郭生梅); Qian B(钱波); Xia CG(夏春谷); Huang HM(黄汉民)
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| 2010 | |
| Source Publication | Chem. Eur. J.
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| ISSN | 0947-6539 |
| Volume | 16Pages:1638-1645 |
| Abstract | A cooperative catalytic system established by the combination of an iron salt and a chiral Brønsted acid has proven to be effective in the asymmetric Friedel–Crafts alkylation of indoles with b-aryl a’-hydroxy enones. Good to excellent yields and enatioselectivities were observed for a variety of a’-hydroxy enones and indoles, particularly for the b-aryl a’-hydroxy enones bearing an electron-withdrawing group at the para position of the phenyl ring (up to 90% yield and 91% ee). The proton of the chiral Brønsted acid, the Lewis acid activation site, as well as the inherent basic site for the hydrogen-bonding interaction of the Brønsted acid are responsible for the high catalytic activities and enantioselectivities of the title reaction. A possible reaction mechanism was proposed. The key catalytic species in the catalytic system, the phosphate salt of FeIII, which was thought to be responsible for the high activity and good enantioselectivity, was then confirmed by ESIMS studies. |
| Keyword | Alkylation Asymmetric Catalysis Brønsted Acids Iron Proton Acceleration |
| Subject Area | 有机功能材料 |
| Funding Organization | the Chinese Academy of Sciences, National Natural Science Foundation of China (nos. 20802085;20625308) |
| Indexed By | SCI |
| Language | 英语 |
| Funding Project | 清洁催化与生物转化研究组 |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/2276 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） |
| Corresponding Author | Xia CG(夏春谷); Huang HM(黄汉民) |
| Recommended Citation GB/T 7714 | Yang L,Zhu QM,Guo SM,et al. Chiral Bronsted Acid Directed Iron-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with β-Aryl α'-Hydroxy Enones[J]. Chem. Eur. J.,2010,16:1638-1645. |
| APA | 杨磊,朱其明,郭生梅,钱波,夏春谷,&黄汉民.(2010).Chiral Bronsted Acid Directed Iron-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with β-Aryl α'-Hydroxy Enones.Chem. Eur. J.,16,1638-1645. |
| MLA | 杨磊,et al."Chiral Bronsted Acid Directed Iron-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with β-Aryl α'-Hydroxy Enones".Chem. Eur. J. 16(2010):1638-1645. |
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| 12_Chem.Eur.J.2010,1（354KB） | 开放获取 | License | View Application Full Text | |||
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