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

页码：973 / 977

页数：5

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