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Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network

Enantiopure cis-1-aminoindan-2-ol was selected as a basic resolving agent for racemic 2-arylalkanoic acids on the basis that its rigid cis-conformation would favor the formation of a supramolecular hydrogen-bonded column, in which chiral discrimination of the racemic carboxylate would occur. It was found that this amino alcohol possesses high resolving efficiency for a variety of racemic acids; also, X-ray crystallographic analyses of the diastereomeric salts showed that a columnar hydrogen-bond network is formed in both the less- and more-soluble diastereomeric salts, as we had expected. A detailed study on the stabilising interactions suggested that there are two that play an important role: (i) hydrogen bonding between the ammonium and hydroxy groups and the acid carboxylate, which determines the formation of the columnar network and (ii) CH…pi, which influences the herringbone packing of the aromatic groups, implying that it also plays some role in chiral discrimination.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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A Carbonylation Approach Toward Activation of Csp2-H and Csp3-H Bonds: Cu-Catalyzed Regioselective Cross Coupling of Imidazo[1,2-a]pyridines with Methyl Hetarenes

An efficient copper-catalyzed selective cross coupling of imidazo[1,2-a]pyridines with methyl hetarenes has been reported. This transformation opened a new route to synthesize the C-3 carbonyl imidazo[1,2-a]pyridine derivative, which is a common structural motif in natural products and pharmaceuticals. 18O-labeling experiments indicated that the oxygen source of products originated from O2.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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cis-1-Amino-2-indanol in asymmetric synthesis. Part I. A practical catalyst system for the enantioselective borane reduction of aromatic ketones

A new class of oxazaborolidine catalysts has been prepared from optically pure cis-1-amino-2 indanols which are available in large quantities. The asymmetric borane reduction of aromatic ketones using these catalysts has been studied.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Reference of 108-47-4, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.108-47-4, Name is 2,4-Dimethylpyridine, molecular formula is C7H9N. In a article£¬once mentioned of 108-47-4

Heterometallic trinuclear {CdII?MII?CdII} pivalates (M = Mg, Ca, or Sr): ways of assembly and structural features

Conditions for chemical assembly of new heterometallic trinuclear pivalates [Cd2M(piv)6L2] (M = Mg, Ca, or Sr; piv is pivalate) were found. Reactions with the nonchelating ligand 2,4-lutidine (lut) gave the crystals of heterometallic complexes [Cd2M(piv)6(lut)2] (M = Mg (1), Ca (2), and Sr (3)). With the chelating ligand 1,10-phenanthroline (phen), only the homometallic dimer [Cd2(piv)4(phen)2] (4) was obtained under these conditions. Yet heterometallic trinuclear complexes with 1,10-phenanthroline ([Cd2Mg(piv)6(H2O)(phen)2] (5), [CaCd2(piv)6(phen)2] (6), and [Cd2Sr(piv)6(phen)2]?2MeCN (7)) were synthesized by reactions of phen with complexes 1?3. For all the complexes obtained, the molecular and crystal structures as well as the details of their molecular architecture were determined. The thermal behavior of aqua complex 5 was studied by TG and DSC. The complex eliminated the water molecule between 130 and 180 C with a high endothermic effect (Q = 101 kJ mol?1) due to (1) intramolecular hydrogen bonds that stabilize its molecular architecture and (2) subsequent structural rearrangements.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Design, synthesis, and evaluation of Leu*Ala hydroxyethylene-based non-peptide beta-secretase (BACE) inhibitors

With the aim of developing small molecular non-peptide beta-secretase (BACE) inhibitors, Leu*Ala hydroxyethylene (HE) was investigated as a scaffold to design and synthesize a series of compounds. Taking advantage of efficient combinatorial synthesis approaches and molecular modeling, extensive structure-activity relationship (SAR) studies were carried out on the N- and C-terminal residues of the Leu*Ala HE scaffold. Isobutyl amine was found to be an optimal C-cap, and suitable hydroxylalkylamines at the 3-position and nitro or methyl(methylsulfonyl)amine at the 5-position of isophthalamide as the N-terminus could form additional hydrogen bonds with BACE active sites and help improve potency. Many new potent non-peptide BACE inhibitors were identified in this study. Among them, compounds 37 and 44 exhibited excellent enzyme-inhibiting potency, comparable to that of OM99-2, and obvious inhibitory effects in cell-based assay with low molecular weights (<600). A reaction mechanism is the microscopic path by which reactants are transformed into products. Each step is an elementary reaction. In my other articles, you can also check out more blogs about 126456-43-7 Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Archives for Chemistry Experiments of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Asymmetric hydrogenation of ketones catalyzed by a ruthenium(ii)-indan- ambox complex

(S,R)-Indan-ambox ligand and its ruthenium(ii) complex have been prepared and successfully applied to asymmetric hydrogenation of prochiral simple ketones. A wide range of unfunctionalized ketones are reduced by Ru(ii)-indan-ambox catalyst with excellent enantioselectivities (up to 97% ee).

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Application of dimedone enamines as dienophiles: stereoselective synthesis of amino enols of fused uracils containing a sugar moiety by hetero-Diels-Alder reactions of barbituric acid 5-ylidene alditols with dimedone enamines

Dimedone enamines were applied for the first time as new dienophiles in hetero-Diels-Alder reactions with inverse electron demand. Cycloadditions of barbituric acid 5-ylidene alditols with dimedone enamines were performed in dichloromethane at room temperature for 3 days and fused uracils-chromeno[2,3-d]pyrimidine-2,4-diones were obtained in good 73-87% yields. Only one enantiomerically pure stereoisomer was obtained in each studied cycloaddition. Analysis of 1H NMR and 2D NMR spectra allowed for the determination that cycloadducts exist in solution as mixture of the neutral form and dipolar ion. The prepared fused uracils contain both amine and enol functional groups, so share amphiprotic properties and they are zwitterions in solid state. The new class of compounds-amino enols was synthesized, which similarly to amino acids exists as zwitterions. In obtained cycloadducts amino groups and sugar moieties are close each other and they both are in cis configuration and in axial position. It was also shown that different alkenes can be used as dienophiles towards barbituric acid 5-ylidene alditols, for example, styrene or 1-amino-2-thiocarbamoyl-cyclopent-1-ene.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Discovery of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Gamma-hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamides and uses thereof

gamma-Hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamide compounds are inhibitors of HIV protease and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described. These compounds are effective against HIV viral mutants which are resistant to HIV protease inhibitors currently used for treating AIDS and HIV infection.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Extended knowledge of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Highly stereoselective asymmetric 6pi-azaelectrocyclization utilizing the novel 7-alkyl substituted cis-1-amino-2-indanols: Formal synthesis of 20-epiuleine

Highly stereoselective asymmetric 6pi-azaelectrocyclization was achieved with generality, based on the reaction between the (E)-3-carbonyl-2,4,6-trienal compounds and the (-)-7-alkyl-cis-1-amino-2-indanol derivatives as the effective novel chiral amines. Furthermore, the chiral auxiliaries of the cyclized products obtained were efficiently removed by the novel manganese dioxide oxidation under remarkably mild conditions, and the method was successfully applied to the formal synthesis of optically active 20-epiuleine. Copyright

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Extracurricular laboratory:new discovery of 2,4-Dimethylpyridine

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Molecular characterization of alkyl nitrates in atmospheric aerosols by ion mobility mass spectrometry

We demonstrate the capability of the ion mobility mass spectrometry (IMS-MS) for molecular characterization of reactive and short-lived alkyl nitrates (ANs) in atmospheric aerosols. We show significantly enhanced sensitivity towards the intact molecules of ANs by ultimately 2 orders of magnitude with the addition of inorganic anions such as chloride and nitrate to the negative electrospray to promote the ion adduct formation. This approach enables the measurement of ANs that have a low tendency to form molecular ions on their own with an improved limit of detection in the range of 0.1 to 4.3muM. Molecular identities of the ANs are well constrained by the developed correlation between the collision cross section and mass-to-charge ratio, which provides a two-dimensional separation of the ONO2-containing compounds on the basis of their molecular size and geometry. Structural information of the nitrate molecules is further probed by the identification of characteristic fragments produced from the collision-induced dissociation of parent AN adducts. Application of the IMS-MS technique is exemplified by the identification of hydroxy nitrates in secondary organic aerosols produced from the photochemical oxidation of isoprene.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis