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学科主题: 金属有机化学
题名: Enantioselective conjugate addition of dialkylzinc and diphenylzinc to enones catalyzed by a chiral copper(I) binaphthylthiophosphoramide or binaphthylselenophosphoramide ligand system
其他题名: 一价铜和硫代膦酰胺或硒代膦酰胺类手性配体催化的金属锌试剂和不饱和酮的不对称加成反应研究
作者: Shi M(施敏) ; Wang CJ(王春江) ; Zhang W(张雯)
通讯作者: 施敏
刊名: Chem.-Eur. J.
发表日期: 2004
卷: 10, 期:21, 页:5507-5516
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实验室
英文摘要: The enantioselective conjugate addition of dialkylzinc or diphenylzinc to enones was catalyzed by a copper(i)-axially chiral binaphthylthiophosphoramide or binaphthylselenophosphoramide ligand system at room temperature (20degreesC) or 0degreesC, affording the Michael adducts in high yields with excellent ee for cyclic and acyclic enones. The enantioselectivity and reaction rate achieved here are one of the best results yet for the Cu-catalyzed conjugate addition to enones. It was revealed that this series of chiral phosphoramides was a novel type of S,N-bidentate ligands on the basis of P-31 NMR and C-13 NMR spectroscopic investigations. The mechanism of this asymmetric conjugate addition system has been investigated as well. We found that the acidic proton of phosphoramide in these chiral ligands play a significant role in the formation of the active species. A bimetallic catalytic process has been proposed on the basis of previous literature. The linear effect of product ee and ligand ee further revealed that the active species is a monomeric Cu-I complex bearing a single ligand [Cu-I:ligand 1:1].
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000224783800025
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/9936
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:
Shi M,Wang CJ,Zhang W. Enantioselective conjugate addition of dialkylzinc and diphenylzinc to enones catalyzed by a chiral copper(I) binaphthylthiophosphoramide or binaphthylselenophosphoramide ligand system[J]. Chem.-Eur. J.,2004,10(21):5507-5516.
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