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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
Shi M(施敏); Wang CJ(王春江); Zhang W(张雯); Shi M(施敏)
2004
发表期刊Chem.-Eur. J.
卷号10期号:21页码:5507-5516
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].
学科领域金属有机化学
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
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收录类别SCI
语种英语
WOS记录号WOS:000224783800025
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被引频次:63[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/9936
专题金属有机化学国家重点实验室
通讯作者Shi M(施敏)
推荐引用方式
GB/T 7714
Shi M,Wang CJ,Zhang W,et al. 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.
APA Shi M,Wang CJ,Zhang W,&施敏.(2004).Enantioselective conjugate addition of dialkylzinc and diphenylzinc to enones catalyzed by a chiral copper(I) binaphthylthiophosphoramide or binaphthylselenophosphoramide ligand system.Chem.-Eur. J.,10(21),5507-5516.
MLA Shi M,et al."Enantioselective conjugate addition of dialkylzinc and diphenylzinc to enones catalyzed by a chiral copper(I) binaphthylthiophosphoramide or binaphthylselenophosphoramide ligand system".Chem.-Eur. J. 10.21(2004):5507-5516.
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