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Relevant academic research and scientific papers

Diamine-Tethered Bis(thiourea) Organocatalyst for Asymmetric Henry Reaction

We have developed a novel multifunctional C2-symmetric biphenyl-based diamine-tethered bis(thiourea) organocatalyst, which was tested in the asymmetric Henry reaction. Under thoroughly optimized conditions, the catalyst provided exceptionally high yields and excellent enantioselectivities especially for electron-deficient aromatic and heterocyclic substrates. Due to a high affinity of the catalyst to silica gel, a simple chromatography-free nitroaldol isolation procedure was feasible. Preliminary kinetic and spectroscopic experiments were performed in order to complete the mechanistic picture of the organocatalyzed nitroaldolization process. Finally, the developed synthetic strategy was successfully applied to the catalytic enantioselective syntheses of enantiopure (S)-econazole and (R)-mirabegron a late-stage intermediate.

Magnetically recoverable catalyst for the asymmetric Henry reaction based on a substituted imidazolidine-4-one copper(II) complex supported by Fe3O4·SiO2 nanoparticles

The preparation and characterization of a heterogeneous recyclable catalyst based on Cu(II) complex of magnetic nanoparticles Fe3O4·SiO2 with (2R,5S)-5-isopropyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one is described.

Albumin-mediated asymmetric nitroaldol reaction of aromatic aldehydes with nitromethane in water

We succeeded in the asymmetric nitroaldol (Henry) reaction of aromatic aldehydes with nitromethane using human serum albumin (HSA) in water at neutral pH. The reaction of 4-nitrobenzaldehyde smoothly proceeded for 24 h at 30 °C to afford the corresponding

Catalytic asymmetric nitroaldol (Henry) reaction with a zinc-fam catalyst

(Chemical Equation Presented) Ferrocenyl-substituted aziridinylmethanol (Fam-1) was used as a catalyst with zinc for the asymmetric nitroaldol (Henry) reaction. This catalyst worked with a variety of aldehydes (aromatic, aliphatic, α,β-unsaturated, and he

Probing the evolution of an Ar-BINMOL-derived salen-Co(iii) complex for asymmetric Henry reactions of aromatic aldehydes: Salan-Cu(ii) versus salen-Co(iii) catalysis

A new type of chiral salen-Co catalyst that features aromatic π-walls and an active Co(iii) center has been developed for enantioselective Henry/nitroaldol reactions on the basis of salen-Cu catalysis. The asymmetric Henry reaction of aromatic aldehydes a

Synthesis of planar chiral [2.2]paracyclophane Schiff bases for the enantioselective Henry reaction

A series of diastereomerically pure Schiff base ligands based on [2.2]paracyclophane backbones were synthesized and separated. The new planar chiral [2.2]paracyclophane Schiff bases were used as ligands in Cu-catalyzed asymmetric Henry reactions with high

Highly enantioselective nitroaldol reactions catalyzed by copper(II) complexes derived from substituted 2-(pyridin-2-yl)imidazolidin-4-one ligands

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

A chiral Cu-salan catalyst with a rotatable aromatic π-wall: Molecular recognition-oriented asymmetric henry transformation of aromatic aldehydes

An aromatic π-wall as a reaction activator and inactivator: A novel salan ligand was prepared from Ph-BINMOL. The derived Cu complex was capable to distinguish benzaldehyde and halide-substituted benzaldehydes from methyl-, methoxy-, hydroxy-, and nitro-s

Synthesis and applications in Henry reactions of novel chiral thiazoline tridentate ligands

Several novel chiral tridentate ligands containing thiazoline were efficiently synthesized from commercially available l=cysteine in high yield. These ligands were subsequently applied to the asymmetric Henry reaction of nitromethane and various aldehydes. It was found that the structures of the thiazoline ligands had a significant influence on the enantioselectivity. It was shown that the optimal catalyst for this reaction was a ligand complexed with CuCl, which was formed from chiral thiazoline with chiral aminoalcohol. At -20°C, with 10 mol% of this ligand, a product with (S)-configuration was isolated in 93% yield and 98% enantiomeric excess.

Highly enantioselective henry reaction catalyzed by C2-symmetric modular BINOL-oxazoline Schiff base copper(II) complexes generated in situ

A 16-member library of C2-symmetric modular chiral BINOL-oxazoline Schiff base copper(II) complex catalysts generated in situ was easily generated in a one-pot, three-component manner. This approach avoided the need for isolation and characteri