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

Citations Over TimeTop 11% of 2011 papers

Abstract

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.

Related Papers

• → Asymmetric Henry reaction catalyzed by chiral secondary diamine-copper(II) complexes(2008)69 cited
• → Formation of multi-stereogenic centers using a catalytic diastereoselective Henry reaction(2010)28 cited
• → Synthesis of chiral 1,2-diamines from α-pinene and their use in asymmetric nitroaldol reaction(2015)11 cited
• → Chiral Cu(II)‐N ₄ Complex Catalyzed Asymmetric Aza‐Henry Reaction and Its Application in the Synthesis of β ‐Diamine(2017)6 cited
• → Enantioselective Nitroaldol (Henry) Reaction of p-Nitrobenzaldehyde and Nitromethane Using a Copper (II) Complex Derived from (R,R)-1,2-Diaminocyclohexane: (1S)-1-(4-Nitrophenyl)-2-nitroethane-1-ol(2013)2 cited