Highly Enantioselective Nitroaldol Reactions Catalyzed by Copper(II) Complexes Derived from Substituted 2-(Pyridin-2-yl)imidazolidin-4-one Ligands

被引：41
|
作者：
Panov, Illia [1 ]
Drabina, Pavel [1 ]
Padelkova, Zdenka [2 ]
Simunek, Petr [1 ]
Sedlak, Milos [1 ]
机构：
[1] Univ Pardubice, Fac Chem Technol, Inst Organ Chem & Technol, Pardubice 53210, Czech Republic
[2] Univ Pardubice, Fac Chem Technol, Dept Gen & Inorgan Chem, Pardubice 53210, Czech Republic
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 11期
关键词：
CU-II; HENRY; SALT;
D O I：
10.1021/jo200703j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ten optically pure substituted 2-(pyridin-2-yl)imidazolidin-4-ones, 1a-d, 2a-4a, and 2b-4b, were prepared and characterized. The absolute configurations of individual ligands were determined by X-ray analysis or NOESY experiments. The Cu(II) complexes of the respective ligands were studied as enantioselective catalysts of the nitroaldol (Henry) reaction of aldehydes with nitromethane, giving the corresponding substituted 2-nitroalkanols. In the case of an anti arrangement of the imidazolidin-4-one ring, the obtained result was 91-96% ee, whereas in the case of syn arrangement, a significant drop to 25-27% ee was observed.
引用
收藏
页码：4787 / 4793
页数：7
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