10.1021/jo200703j.s003
Illia Panov
Illia
Panov
Pavel Drabina
Pavel
Drabina
Zdeňka Padělková
Zdeňka
Padělková
Petr Šimůnek
Petr
Šimůnek
Miloš Sedlák
Miloš
Sedlák
Highly Enantioselective Nitroaldol Reactions Catalyzed by Copper(II) Complexes Derived from Substituted 2-(Pyridin-2-yl)imidazolidin-4-one Ligands
American Chemical Society
2011
LigandsTen
imidazolidin
ligand
Derived
complex
Pyridin
aldehyde
Enantioselective Nitroaldol Reactions Catalyzed
nitromethane
nitroaldol
Substituted
ee
Complexe
pyridin
Henry
configuration
enantioselective catalysts
analysis
syn arrangement
nitroalkanol
NOESY experiments
Cu
2011-06-03 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Highly_Enantioselective_Nitroaldol_Reactions_Catalyzed_by_Copper_II_Complexes_Derived_from_Substituted_2_Pyridin_2_yl_imidazolidin_4_one_Ligands/2645200
Ten optically pure substituted 2-(pyridin-2-yl)imidazolidin-4-ones, <b>1a</b>–<b>d</b>, <b>2a</b>–<b>4a</b>, and <b>2b</b>–<b>4</b><b>b</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.