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

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posted on 03.06.2011, 00:00 by Illia Panov, Pavel Drabina, Zdeňka Padělková, Petr Šimůnek, Miloš Sedlák
Ten optically pure substituted 2-(pyridin-2-yl)imidazolidin-4-ones, 1ad, 2a4a, and 2b4b, 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.