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

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Complexes of the type [Pt(L)Cl3]- (L = pyridine derivative) were synthesized and studied by 13C and 195Pt NMR spectroscopies. The 195Pt signals were observed between -1720 and -1897 ppm. No correlation between the delta(Pt) and the pKa of the protonated pyridine derivatives was found. The chemical shifts vary with the substituents on the pyridine ligand. Compounds with substituents in ortho positions were observed at lower fields, except for complexes containing hydroxy or amine groups. The latter compounds were observed at higher fields, close to the signals of the Pt-unsubstituted pyridine compound. These results were explained in terms of the solvent effect. The chemical shifts delta(C) and the coupling constants J(13C-195Pt) were measured and the results interpreted with a view of obtaining information on the nature of the Pt – N bond. The possibility of pi-bonding between platinum and the pyridine ligand is examined. The conformation of the pyridine ring in relation to the platinum plane and the energies of the rotation barriers around the Pt – N bond in these types of platinum(II) complexes are briefly discussed. The crystal structure of trans-Pt(2,6-(HOCH2)2py)2Cl2-2H 2-O was determined by X-ray diffraction. The compound is monoclinic, C2/m, a = 7.022(6), b = 15.646(13), c = 8.344(10) A, ss= 93.35(8), Z = 2, R = 0.037. The platinum atom is located at the junction of the twofold axis and the mirror plane, the N atoms and the para-C atom of the pyridine ring are situated on the twofold axis, and the chloride ligands are on the mirror plane. The compound crystallizes with molecules of water, which are H-bonded to the hydroxy groups. The Pt – Cl bond distance is 2.306(2) A, and that of the Pt – N bond is 2.041(6) A. The dihedral angle between the platinum and the pyridine planes is 79.8.

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

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A series of 1?-(6-aminopurin-9-yl)-1?-deoxy-N-methyl-beta-D-ribofuranuronamides that were characterised by 2-dialkylamino-7-methyloxazolo[4,5-b]pyridin-5-ylmethyl substituents on N6 of interest for screening as selective adenosine A3 receptor agonists, have been synthesised. This work involved the synthesis of 2-dialkylamino-5-aminomethyl-7-methyloxazolo[4,5-b]pyridines and analogues that were coupled with the known 1?-(6-chloropurin-9-yl)-1?-deoxy-N-methyl-beta-D-ribofuranuronamide. The oxazolo[4,5-b]pyridines were synthesized by regioselective functionalisation of 2,4-dimethylpyridine N-oxides. The regioselectivities of these reactions were found to depend upon the nature of the heterocycle with 2-dimethylamino-5,7-dimethyloxazolo[4,5-b]pyridine-N-oxide undergoing regioselective functionalisation at the 7-methyl group on reaction with trifluoroacetic anhydride in contrast to the reaction of 4,6-dimethyl-3-hydroxypyridine-N-oxide with acetic anhydride that resulted in functionalisation of the 6-methyl group. To optimise selectivity for the A3 receptor, 5-aminomethyl-7-bromo-2-dimethylamino-4-[(3-methylisoxazol-5-yl)methoxy]benzo[d]oxazole was synthesised and coupled with the 1?-(6-chloropurin-9-yl)-1?-deoxy-N-methyl-beta-D-ribofuranuronamide. The products were active as selective adenosine A3 agonists.

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

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An efficient and regioselective introduction method of 2-methylpyridines to the secondary position of Baylis-Hillman adducts has been developed. A base treatment of 2-methylpyridinium salt of Baylis-Hillman bromide generated N-allylenamine intermediate which underwent a facile 3-aza-Cope rearrangement under mild conditions to produce the product.

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

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The CuII atom of the title complex, [Cu(C9H7NO3)-(C7H 9N)(H2O)], has a square-pyramidal coordination sphere with a tridentate N-salicylideneglycinato Schiff base dianion and a 2,4-dimethylpyridine ligand bound in the basal plane. The apex of the pyramid is occupied by an O atom from the coordinated water molecule at an apical distance of 2.416 (2) A. The monomeric moieties in the crystal are stabilized through hydrogen bonding, building a two-dimensional network. The copper(II) polyhedra are arranged in two magnetically inequivalent orientations, leading to a slightly distorted ferrodistortive coupled g tensor.

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

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Arenastatin A (1, cryptophycin 24) was synthesized by convergence of hydroxy ester 16 with amino acid derivative 27; two independent and highly efficient routes to 16 are disclosed.

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

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A cationic degradation product, formed in solution from retinal Schiff base (RSB), is examined in the gas phase using ion mobility spectrometry, photoisomerization action spectroscopy, and collision induced dissociation (CID). The degradation product is found to be N-n-butyl-2-(beta-ionylidene)-4-methylpyridinium (BIP) produced through 6pi electrocyclization of RSB followed by protonation and loss of dihydrogen. Ion mobility measurements show that BIP exists as trans and cis isomers that can be interconverted through buffer gas collisions and by exposure to light, with a maximum response at lambda = 420 nm. Graphical Abstract[Figure not available: see fulltext.]

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

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A number of CF3-substituted carbinols decorated with an azine donor are efficiently prepared from fluoral and kinetically resolved in a reagent-controlled, Cu-H-catalysed Si-O coupling with a chiral silane. Selectivity factors are high, indicating a larger steric effect than CH 3 or C6H5 groups.

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

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The compounds are substituted isocytosines which are histamine H 2-antagonists. Two specific compounds of the present inventon are 2-2-(5-methyl-4-imidazolylmethylthio)ethylamino!-5-(3-pyridylmethyl)-4-pyrimi done and 2-2-(3-bromo-2-pyridylmethylthio)ethylamino!-5-(4-pyridylmethyl)-4-pyrimidone .

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

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Ion mobility spectrometry (IMS) is an analytical technique used for fast and sensitive detection of illegal substances in customs and airports, diagnosis of diseases through detection of metabolites in breath, fundamental studies in physics and chemistry, space exploration, and many more applications. Ion mobility spectrometry separates ions in the gas-phase drifting under an electric field according to their size to charge ratio. Ion mobility spectrometry disadvantages are false positives that delay transportation, compromise patient’s health and other negative issues when IMS is used for detection. To prevent false positives, IMS measures the ion mobilities in 2 different conditions, in pure buffer gas or when shift reagents (SRs) are introduced in this gas, providing 2 different characteristic properties of the ion and increasing the chances of right identification. Mobility shifts with the introduction of SRs in the buffer gas are due to clustering of analyte ions with SRs. Effective SRs are polar volatile compounds with free electron pairs with a tendency to form clusters with the analyte ion. Formation of clusters is favored by formation of stable analyte ion-SR hydrogen bonds, high analytes’ proton affinity, and low steric hindrance in the ion charge while stabilization of ion charge by resonance may disfavor it. Inductive effects and the number of adduction sites also affect cluster formation. The prediction of IMS separations of overlapping peaks is important because it simplifies a trial and error procedure. Doping experiments to simplify IMS spectra by changing the ion-analyte reactions forming the so-called alternative reactant ions are not considered in this review and techniques other than drift tube IMS are marginally covered.

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