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

页码：4787 / 4793

页数：7

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