Highly Enantioselective Nitroaldol Reactions Catalyzed by Copper(II) Complexes Derived from Substituted 2-(Pyridin-2-yl)imidazolidin-4-one Ligands
Authors:
- 2 May 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (11) , 4787-4793
Abstract
Ten optically pure substituted 2-(pyridin-2-yl)imidazolidin-4-ones, 1a–d, 2a–4a, and 2b–4 b, 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.Keywords
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