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学科主题: 金属有机化学
题名: Controllable enantioselective Friedel-Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo-C-3-symmetric trisoxazoline copper(II) complexes
其他题名: 通过假C3-对称的三恶唑啉铜络合物催化的吲哚与亚烷基丙二酸酯的可控的对应选择性傅克反应
作者: Zhou J(周剑) ; Ye MC(叶萌春) ; Huang ZZ(黄铮铮) ; Tang Y(唐勇)
通讯作者: 唐勇
刊名: J. Org. Chem.
发表日期: 2004
卷: 69, 期:4, 页:1309-1320
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所金属有机化学国家重点实验室
英文摘要: Pseudo-C-3-symmetric trisoxazoline copper(II) complexes prove to be excellent catalysts in the Friedel-Crafts alkylation of indoles with alkylidene malonates. The absolute stereochemistry of this reaction is shown to be dependent on the solvent. Reactions in isobutyl alcohol afford the Friedel-Crafts alkylation adducts in excellent yields and with up to +98% ee. In 1,1,2,2-tetrachloroethane (TTCE), however, the opposite enantiomers of the products are obtained in good yields with up to -89% ee. Water tolerance of chiral catalyst trisoxazoline 2a/Cu(OTf)(2) is examined, and it is found that the addition of up to 200 equiv of water relative to catalyst in isobutyl alcohol has almost no effect on enantioselectivity but slows down the reaction. The reaction scope is studied as well. The roles of alcohol as the solvent to accelerate the reaction are discussed. The stereochemical models of asymmetric induction for reactions both in isobutyl alcohol and in TTCE are also developed.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000188955400039
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/19293
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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Recommended Citation:
Zhou J,Ye MC,Huang ZZ,et al. Controllable enantioselective Friedel-Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo-C-3-symmetric trisoxazoline copper(II) complexes[J]. J. Org. Chem.,2004,69(4):1309-1320.
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