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Relevant academic research and scientific papers

Binaphthyl-based chiral bifunctional organocatalysts for water mediated asymmetric List-Lerner-Barbas aldol reactions

Novel binaphthyl-based chiral bifunctional organocatalysts were designed, synthesized and successfully applied to the asymmetric List-Lerner-Barbas aldol reaction in the presence of water. These organocatalysts were found to be effective catalysts for the

Pyrimidine-derived prolinamides as recoverable bifunctional organocatalysts for enantioselective inter- and intramolecular aldol reactions under solvent-free conditions

Chiral L-prolinamides 2 containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-pyrimidinyl unit are synthesized and used as general organocatalysts for intermolecular and intramolecular aldol reactions with 1,6-hexanedioic acid as a co-catalyst under solvent-free conditions. The intermolecular reaction between ketone-aldehyde and aldehyde-aldehyde must be performed under wet conditions with catalyst (S,S)-2b at 10 °C, which affords anti-aldols with high regio-, diastereo-, and enantioselectivities. For the Hajos-Parrish-Eder-Sauer-Wiechert reaction, both diastereomers of catalyst 2 give similar results at room temperature in the absence of water to give the corresponding Wieland-Miescher ketone and derivatives. Both types of reactions were scaled up to 1 g, and the organocatalysts were recovered by extractive workup and reused without any appreciable loss in activity. DFT calculations support the stereochemical results of the intermolecular process and the bifunctional role played by the organocatalyst by providing a computational comparison of the H-bonding networks occurring with catalysts 2a and 2b. The intermolecular ketone-aldehyde and aldehyde-aldehyde aldol reactions and the Hajos-Parrish-Eder-Sauer-Wiechert versions with the employment of chiral L-prolinamides containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-pyrimidinyl unit are successfully performed under solvent-free conditions; WMK = Wieland-Miescher ketone.

Novel chiral bifunctional L-thiazoline-amide derivatives: Design and application in the direct enantioselective aldol reactions

Several novel chiral bifunctional l-thiazoline-amide derivatives were simply synthesized from commercially available l-cysteine and l-proline in high yield. These catalysts were subsequently applied to the direct enantioselective aldol reactions of variou

Evaluation of mono- and dipeptides as organocatalysts for enantioselective aldol reaction

Catalytic activities of (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (THIQA)-based mono- and dipeptides and their l-proline analogs in asymmetric aldol reaction were investigated. THIQA-based dipeptides showed better enantioselectivity than proli

Four metalloporphyrinic frameworks as heterogeneous catalysts for selective oxidation and aldol reaction

Four porous metalloporphyrinic framework materials, [(CH3) 2NH2][Zn2(HCOO)2(Mn III-TCPP)]·5DMF·2H2O (1; H6TCPP = tetrakis(4-carboxyphenyl)porphyrin), [(CH3)2NH 2][Cd2(HCOO)2(MnIII-TCPP)] ·5DMF·3H2O (2), [Zn2(HCOO)(Fe III(H2O)-TCPP)]·3DMF·H2O (3), and [Cd3(H2O)6(μ2-O)(Fe III-HTCPP)2]·5DMF (4) were synthesized by heating a mixture of MIIICl-H4TCPP (M = Mn and Fe) and M′ (M′ = Zn or Cd) nitrate in a mixed solvent of DMF and acetic acid. Compounds 1-3 are built up from M′2(COO)4 paddle-wheel subunits bridged by MIII-TCPP and formate ligands to form their 3D connections. The formate pillar heterogeneously connects with M and M′ cations in 1 and 2 and homogeneously joins M′ cations in 3. The μ2-O bridged FeIII-HTCPP dimer performs as a decadentate ligand to link 10 cadmium cations for the formation of an interesting 3D coordination network of 4. The four porphyrinic frameworks present interesting catalytic properties in the selective epoxidation of olefins, oxidation of cyclohexane, and intermolecular aldol reaction of aldehydes and ketones.

Antibody-catalyzed decarboxylation and aldol reactions using a primary amine molecule as a functionalized small nonprotein component

Catalytic antibody 27C1 bears binding sites for both a substrate- and a functionalized small nonprotein component in the active site. We investigated the possibility of exploiting imine and enamine intermediates using a primary amine molecule into the act

Recoverable silica-gel supported binam-prolinamides as organocatalysts for the enantioselective solvent-free intra- and intermolecular aldol reaction

Silica-gel supported binam-derived prolinamides are efficient organocatalysts for the direct intramolecular and intermolecular aldol reaction under solvent-free conditions using conventional magnetic stirring. These organocatalysts in combination with benzoic acid showed similar results to those obtained under similar homogeneous reaction conditions using an organocatalyst of related structure. For the intermolecular process, the aldol products were obtained at room temperature and using only 2 equiv of the ketone with high yields, regio-, diastereo- and enantioselectivities. Under these reaction conditions, also the cross aldol reaction between aldehydes is possible. The recovered catalyst can be reused up to nine times providing similar results. More interestingly, these heterogeneous organocatalysts can be used in the intramolecular aldol reaction allowing the synthesis of the Wieland-Miescher and ketone analogues with up to 92% ee, with its reused being possible up to five times without detrimental on the obtained results.

Efficient asymmetric aldol reaction catalyzed by polyvinylidene chloride-supported ionic liquid/l-proline catalyst system

A series of polyvinylidene chloride (PVDC)-supported ionic liquids were derived from 4-dimethylaminopyridine and used together with l-proline in water as efficient asymmetric organocatalysts for direct asymmetric aldol reactions between cyclohexanone and

Stereoselective synthesis of vic-halohydrins via l-tert-leucine-catalyzed syn-selective aldol reaction

L-tert-Leucine was found to be an effective organocatalyst for the asymmetric aldol reaction of chloroacetone. The stereoselective synthesis of vic-halohydrins was accomplished with excellent regioselectivity (>99%) to generate α-chloro-β-hydroxy ketones

Asymmetric aldol reaction catalyzed by modularly designed organocatalysts

The self-assembly of the precatalyst modules, which are amino acids and cinchona alkaloid derivatives, leads to the direct formation of the desired organocatalysts without any synthesis. These modularly designed organocatalysts (MDOs) may be used for cata