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Relevant academic research and scientific papers

Recyclable Enantioselective Catalysts Based on Copper(II) Complexes of 2-(Pyridine-2-yl)imidazolidine-4-thione: Their Application in Asymmetric Henry Reactions

This paper describes the preparation of enantioselective catalysts based on derivatives of imidazolidine-4-thione and their subsequent anchoring by means of a sulfur atom on a polymeric carrier. First, we verified the catalytic activity and enantioselecti

(S)-Pyrrolidine-containing chiral manganese(III)-salalen and -salan complexes as catalysts for the asymmetric henry reaction

Chiral Mn(III)-salalen and -salan complexes derived from (S)-proline have been used as catalysts for the asymmetric Henry (nitro-aldol) reaction. We have also used this methodology for a variety of substrates to afford nitroaldol products in 40-94% yields

Catalytic asymmetric henry reaction of nitroalkanes and aldehydes catalyzed by a chiral N, N '-dioxide/Cu(I) complex

An easily available N,N'-dioxide/Cu(I) complex has been developed for the catalytic asymmetric nitroaldol (Henry) reaction of aldehydes with nitroethane. Under mild reaction conditions, a series of substituted aromatic, heteroaromatic and α,β-unsaturated

Polytopic bis(oxazoline)-based ligands for recoverable catalytic systems applied to the enantioselective Henry reaction

Several kinds of polytopic chiral ligands (including ditopic, tritopic and tetratopic), based on the bis(oxazoline) and azabis(oxazoline) motifs, have been tested in the preparation of recoverable catalytic systems for the Henry reaction. The results obta

Design of a chiral secondary amine ligand for copper-catalyzed anti -selective Henry reaction

A series of chiral binaphthyl-containing diphenylethylenediamine (binaph-dpen) ligands was designed and synthesized for the copper-catalyzed asymmetric Henry reaction. The N-monobenzyl (S)-binaph-(R,R)-dpen ligand, with a secondary amine portion, promoted

Asymmetric Henry reactions of aldehydes with various nitroalkanes catalyzed by copper(II) complexes of novel chiral N-monoalkyl cyclohexane-1,2-diamines

A number of novel chiral diamines 3, (1R,2R)-N-monoalkylcyclohexane-1,2- diamines, were designed and synthesized from trans-cyclohexane-1,2-diamine and applied to the catalytic asymmetric Henry reaction of benzaldehyde and nitromethane to provide β-nitroa

Enantiocatalytic activity of substituted 5-benzyl-2-(pyridine-2-yl) imidazolidine-4-one ligands

Currently, asymmetric synthesis represents one of the main streams of organic synthesis. Although an extensive research has been carried out in this area, the synthesis of chiral compounds with the required enantiomeric purity is still a challenging issue. Herein, we focus on the preparation of new enantioselective catalysts based on pyridine-imidazolidinones. The substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-ones 5-8 were prepared by condensation of chiral amino acid amides (α-methylDOPA and α- methylphenylalanine) with 2-acetylpyridine and pyridine-2-carbaldehyde. The individual isomers of the described ligands 5-8 were separated chromatographically. The copper(II) complexes of these chiral ligands were studied as enantioselective catalysts for the asymmetric Henry reaction of substituted aldehydes with nitromethane or nitroethane. The ligands containing a methyl group at the 2-position of the imidazolidinone ring 6a and 8a exhibit a high degree of enantioselectivity (up to 91% ee). The nitroaldols derived from nitroethane (2-nitropropan-1-ols) were obtained with a comparable enantiomeric purity to derivatives of 2-nitroethanol. This group of ligands represents a new and promising class of enantioselective catalysts, which deserve further attention.

Copper complex of aminoisoborneol schiff base Cu2(SBAIB-d) 2: An efficient catalyst for direct catalytic asymmetric nitroaldol (henry) reaction

A new bifunctional copper complex of the aminoisoborneol Schiff base - Cu2(SBAIB-d)2 - has been developed for the effective direct catalytic asymmetric Henry reaction. One mol% of this catalyst produces the expected Henry products in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee). The utility of the present catalyst was also extended to the Henry reaction with nitroethane and 1-nitropropane that furnished the corresponding products in moderate to high yields (up to 99%) with moderate to high enantioselectivities of syn (up to 98% ee) and anti (up to 98% ee) diastereomers. The highlights of this catalytic system are easy manipulation, air and moisture tolerance, the need for 1 mol% of an easily synthesizable catalyst and the high enantioselectivities achieved for a wide range of substrates. Copyright

Bis(oxazoline)-based coordination polymers: A recoverable system for enantioselective Henry reactions

An efficient release-capture strategy for the recovery and reuse of enantioselective catalysts in the Henry reaction is described. This strategy is based on the precipitation of an insoluble coordination polymer at the end of each reaction, allowing easy

Urea/transition-metal cooperative catalyst for anti-selective asymmetric nitroaldol reactions

A cooperative catalyst that features urea H-bonding and a cobalt center was developed for anti-selective asymmetric Henry reactions (see scheme). The H-bonds of urea play a crucial role in the improvement in yield (from 30 % to 84 %), enantioselectivity (