Asymmetric Conjugate Addition to Cyclic Enone Catalyzed by Cu-NHC Complexes with C2 Symmetry

被引：8
|
作者：
Shan Fengjun [1 ]
Jiang Lan [1 ,3 ]
Li Zhengning [1 ,2 ]
Zhao Defeng [3 ]
机构：
[1] Dalian Univ, Coll Environm & Chem Engn, Dalian 116622, Liaoning, Peoples R China
[2] Dalian Univ, Liaoning Key Lab Bioorgan Chem, Dalian 116622, Liaoning, Peoples R China
[3] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Liaoning, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2011年 / 29卷 / 05期
基金：
中国国家自然科学基金;
关键词：
asymmetric catalysis; copper-NHC; imidazolinium salt; C-2; symmetry; Michael addition; QUATERNARY STEREOGENIC CENTERS; HETEROCYCLIC CARBENE COMPLEXES; ENANTIOSELECTIVE SYNTHESIS; STEREODIRECTING LIGANDS; REAGENTS; DESIGN; SUZUKI;
D O I：
10.1002/cjoc.201190198
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A series of chiral, C-2 symmetric tridentate N-heterocyclic carbene precursors, containing two N-functionalized hydroxyl or alkoxyl groups, were synthesized. They were applied to catalyze the asymmetric conjugate addition of diethylzinc to cyclohex-2-enone and cyclopent-2-enone. Enantioselectivity of corresponding reactions can be accomplished with up to 76% ee, and 65% ee, respectively. Flip of major enantiomer was observed when different bases or copper sources were utilized.
引用
收藏
页码：973 / 977
页数：5
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