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Henry reaction catalyzed by chiral copper(II) complexes derived from 2-(pyridin-2-yl)-1H-imidazolidin-4-one ligands

Authors: Drabina Pavel | Sedlák Miloš

Year: 2014

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Henry reaction catalyzed by chiral copper(II) complexes derived from 2-(pyridin-2-yl)-1H-imidazolidin-4-one ligands	Nitrogen ligands and their transition metal complexes belong among compounds widely used as homogeneous catalysts in many chemical processes. The nitrogen ligand containing stereogenic centre can be used as enantioselective catalyst for an asymmetric reaction. Therefore, we have recently developed several series of chiral 2-(pyridin-2-yl)-1H-imidazolidin-4-one derivatives (Fig. 1) with the aim to study their catalytic activity in various processes including asymmetric reactions. We found out that the copper(II) acetate complexes of these ligands are highly enantioselective catalysts for Henry reaction (ee up to 96% ee). In our most recent investigation, we dealt with the structure modification of 2-(imidazolidinyl)pyridine derivatives on stereogenic centres to study the influence of ligand design on enantiocatalytic activity in Henry reaction. We found that ligands with trans-arrangement are generally more efficient than appropriate cis-derivatives. Surprisingly, the ligands with quarternary stereogenic centres derived from α-methylated 2-aminoacids are more enantioselective than the ligands derived from coded 2-aminoacids. Moreover, these ligands are more resistant to oxidation and racemization. The most efficient catalysts were used for syntheses of key intermediates of the important pharmaceutical substances (Salmeterol, Amprenavir). Presented results indicate that this group of imidazolidinones represents new promising branch of enantioselective catalysts.	Henry reaction; catalysis; complexes; 2-pyridin-2-yl-1H-imidazolidin-4-one