Chiral Bronsted Acid Directed Iron-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with β-Aryl α'-Hydroxy Enones

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	Chiral Bronsted Acid Directed Iron-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with β-Aryl α'-Hydroxy Enones
	Huang HM(黄汉民); Huang HM(黄汉民); Yang L(杨磊); Xia CG(夏春谷); Qian B(钱波)
刊名	Chem. Eur. J.
	2010
卷号	16 页码:1638-1645
关键词	alkylation asymmetric catalysis Brønsted acids iron proton acceleration
ISSN号	0947-6539
通讯作者	夏春谷 ; 黄汉民
中文摘要	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.
学科主题	有机功能材料
收录类别	SCI
资助信息	the Chinese Academy of Sciences, National Natural Science Foundation of China (nos. 20802085;20625308)
语种	英语
公开日期	2012-11-30
内容类型	期刊论文
源URL	[http://210.77.64.217/handle/362003/2276]
专题	兰州化学物理研究所_OSSO国家重点实验室
通讯作者	Huang HM(黄汉民); Huang HM(黄汉民); Xia CG(夏春谷)
推荐引用方式 GB/T 7714	Huang HM,Huang HM,Yang L,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	黄汉民,黄汉民,杨磊,夏春谷,&钱波.(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	黄汉民,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.