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学科主题: 金属有机化学
题名: Importance of planar chirality in chiral catalysts with three chiral elements: The role of planar chirality in 2'-substituted 1,1'-P,N-ferrocene ligands on the enantioselectivity in Pd-catalyzed allylic substitution
其他题名: 平面手性在具有三种手性元素的手性配体中的重要性: 2'-取代-1,1'-P,N-二茂铁配体中平面收性在钯催化丙基取代反应的对映选择性中的作用
作者: Deng WP(邓卫平) ; You SL(游书力) ; Hou XL(侯雪龙) ; Dai LX(戴立信) ; Yu YH(余亦华) ; Xia Y(夏蔚) ; Sun J(孙杰)
通讯作者: 侯雪龙
刊名: J. Am. Chem. Soc.
发表日期: 2001-01-01
卷: 123, 期:27, 页:6508-6519
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开放实验室
英文摘要: A series of novel panar chiral 2'-substituted 1,1'-P,N-ferrocene ligands 9-11, 14, and 16 were prepared with diastereopurity >99:1 and found to be effective in asymmetric allylic alkylation and amination reactions. Ligand 14 furnished the highest enantiomeric excess, 98.5% and 96.5% ee in alkylation and amination reactions, respectively. The role of planar chirality in asymmetric reactions has been examined and decisive effects on enantioselectivity as well as the control of absolute configuration in palladium-catalyzed allylic alkylation and amination reactions were observed. To clarify why and how the planar chirality governed the stereochemical outcome, X-ray crystallographic structures of η~3-diphenylallyl Pd complexes, ~1H NMR , ~31P NMR spectra of palladium dichloride complexes, and η~3-diphenylaalyl Pd complexes of three 1,1'-P,N-ferrocene ligands were analyzed with the aid of COSY and 2D NOESY experiments. All results led to the conclusion that planar chirality influences the stereochemical outcome by changing or even inverting the ratio of two rotamers because of the steric interaction between a planar chiral group and the coordination site.
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/15853
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:
Deng WP,You SL,Hou XL,et al. Importance of planar chirality in chiral catalysts with three chiral elements: The role of planar chirality in 2'-substituted 1,1'-P,N-ferrocene ligands on the enantioselectivity in Pd-catalyzed allylic substitution[J]. J. Am. Chem. Soc.,2001,123(27):6508-6519.
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