Henry Reaction Of Nitromethane Research Articles

Synthesis and Catalytic Application of Two Mononuclear Complexes Bearing Diethylenetriamine Derivative Ligand.

Two mononuclear zero-dimensional Ni(II) and Zn(II) complexes bearing diethylenetriamine derivative ligand, namely [NiL(CH3COO)2(H2O)] (1) and [ZnL(CH3COO)2] (2) [L = N, N’-bis(2-hydroxybenzyl)diethylenetriamine], were synthesized under reflux conditions. The molecular composition and structure of the complexes were identified by IR, PXRD, elemental analyses, and single crystal X-ray diffraction. Complex 1 belongs to a monoclinic crystal system with the P21/n space group, and Complex 2 belongs to a monoclinic crystal system with the C2/c space group. The Henry reaction of nitromethane with aromatic aldehydes was explored with Complexes 1 and 2 as the catalyst. Results from the catalytic reaction revealed that the complexes displayed excellent catalytic activities under the optimized conditions and that the substrate scope of aromatic aldehydes could be extended to a certain extent. In addition, the possible catalytic mechanism of the Henry reaction was also deduced.

Two Coordination Compounds Bearing Bis(2-dimethylaminoethyl) Ether: Syntheses, Crystal Structures and Catalytic Application to the Henry Reaction

Two novel coordination compounds, namely [Cu2(BDMAEE)(CH3COO)4] n (1) and [Ni(BDMAEE)Cl2](2) [BDMAEE=bis(2-dimethylaminoethyl) ether], have been synthesized and characterized by IR, elemental analysis, PXRD and X-ray single crystal diffraction. In compound 1, the central Cu(II) ion is coordinated with four oxygen atoms and one nitrogen atom, forming a distorted square pyramidal geometry. The asymmetric units composed of one Cu(II) ion, two acetates and a half of BDMAEE are connected to form an infinite 1D chain structure by the bridging acetate and the BDMAEE. In compound 2, the central Ni(II) ion is coordinated with one oxygen atom, two chlorine anions and two nitrogen atoms, forming a distorted square pyramidal geometry. The compounds exhibited excellent catalytic properties in the Henry reaction of nitromethane with some aromatic aldehydes, and the optimized reaction conditions were obtained.

ChemInform Abstract: Enantioselective Cu(II)‐Catalyzed Henry Reactions with Chiral Cyclohexane‐Based Amidophosphine Ligands.

Abstract Copper-catalyzed asymmetric Henry reactions are described. Using a new chiral amidophosphine ligand, the Henry reaction of nitromethane and various aldehydes proceeded smoothly to provide chiral β-nitroalcohols in reasonable yields (up to 98%) with high enantioselectivity (up to 97% ee).

Enantioselective Cu(II)-catalyzed Henry reactions with chiral cyclohexane-based amidophosphine ligands

Copper-catalyzed asymmetric Henry reactions are described. Using a new chiral amidophosphine ligand, the Henry reaction of nitromethane and various aldehydes proceeded smoothly to provide chiral β-nitroalcohols in reasonable yields (up to 98%) with high enantioselectivity (up to 97% ee).

ChemInform Abstract: 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. Copyright © 2015 John Wiley & Sons, Ltd.

Synthesis of Stable Acyclic Aminals Derived from L-(+)-Aspartic Acid and Their Application in Asymmetric Henry Reactions

Abstract A series of stable acyclic aminals derived from L-(+)-aspartic acid were synthesized in excellent yields (up to 96%) and characterized by spectroscopic methods. They were applied as enantioselective catalysts in Henry reactions of nitromethane with various aldehydes in the presence of Cu(II) ions, affording the corresponding adducts in high yields (up to 90%) and enantioselectivities (up to 92% ee).

ChemInform Abstract: Crown Ether Complex Cation Ionic Liquids: Preparation and Applications in Organic Reactions.

AbstractVarious 18‐crown‐6 and 15‐crown‐5 salts are applied as catalysts and ionic solvents in the Michael addition of alkenes and nucleophiles, Henry reaction of nitromethane with aldehydes, Knoevenagel reaction of malonitrile with aromatic aldehydes.

A New Way to tert-Butyl [(4R,6R)-6-Aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a Key Intermediate of Atorvastatin Synthesis

A new synthesis of tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a key intermediate of the synthesis of an effective HMG-CoA reductase inhibitor atorvastatin, is described. The synthesis is based on the Henry reaction of nitromethane and tert-butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl] acetate. The formed nitroaldol was then O-acetylated and the sodium borohydride reduction of the intermediate provided tert-butyl [(4R,6R)-2,2-dimethyl-6-nitroethyl-1,3-dioxan-4-yl] acetate. Catalytic hydrogenation of the nitro group led to the title compound.