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Enantiomeric purities of axially chiral biaryls with hydroxyl, amino, and carboxyl groups can be easily determined by pmr spectra using MTPA derivatives and shift reagent.

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Reference:
Chiral Catalysts,
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Whereas the Cu(II)-mediated oxidative coupling of 2-aminonaphthalenes 7a and 7b results in the clean formation of 1,1?-binaphthyls 13a and 13b, respectively, their higher homologues and congeners 8 – 12 have been found to exhibit a different reaction pattern. Thus, 2-aminoanthracene (8) gave a ?1:1 mixture of the expected bianthryl derivative 15 and the carbazole 16, whereas the 9-aminophenanthrene (10), 3-phenyl-1-aminonaphthalene (11), and 2-aminochrysene (12) produced almost exclusively the corresponding carbazoles 19, 20, and 21, respectively. By contrast, the isomeric 3-aminophenanthrene (9) gave rise to the azo compound 17 as a result of the preferential oxidation on the nitrogen. The carbazoles have been shown to arise directly from the coupling reactions rather than from the primarily formed binaphthyls. Alternatively, carbazole 19 can also be prepared from 1b on reaction with hydrazine. On the other hand, treatment of 3a with hydrazine resulted in the formation of a ?2:7 mixture of amine 11 and arylhydrazine 22. 2,2?-Diamino-1,1?-bianthryl (15) has been resolved into enantiomers via Cocrystallization with (-)-N-benzylcinchonidinium chloride and shown to have (R)-(-)-15 configuration by X-ray crystallography.

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Chiral Catalysts,
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A palladium-catalysed aminocarbonylation of a steroidal iodoalkene (17-iodo-5alpha-androst-16-ene) model compound with 2,2?-diamino-1,1?-binaphthalene as an N-nucleophile was carried out. The combination of a steroidal skeleton possessing central elements of chirality and a binaphthyl moiety with axial chirality was carried out resulting in a novel type of steroidal carboxamides. The binaphthalene – steroid conjugates are potential 5alpha-reductase inhibitors. Both epimers of the monocarboxamide and those of the dicarboxamide, formed with moderate diastereoselectivity, were isolated and fully characterised.

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Chiral Catalysts,
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A protocol was developed for the solution-phase synthesis of multigram amounts of two 9-fluorenylmethoxycarbonyl (Fmoc)-protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution-phase-synthesized tetraproline CSPs with that prepared by stepwise solid-phase synthesis revealed that all three had similar chromatographic performance for resolving 53 model analytes. This suggests that the solution-phase synthesis of oligoprolines, which allows for the specific benefits of good batch reproducibility, selector homogeneity, and possibly low cost, is a feasible alternative to the solid-phase synthesis of oligoproline CSPs. Copyright

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Chiral Catalysts,
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A short approach to chiral diaza-olefines from protected 2,2?-diamino-1,1?-binaphthyl is presented. Cis- and trans-olefines can be selectively obtained by twofold N-allylation followed by RCM or by bridging a 2,2?-diamino-1,1?-binaphthyl precursor with trans-1,4-dibromo-2-butene. Deprotection afforded cis- and trans-dihydro[1,6]diazecines 1 in 58 and 64% overall yield. The reactivity of the but-2-ene-1,4-diyl fragment was investigated yielding corresponding epoxides, diols, and mono- and dibromo products. In several cases rearrangements and participation of the proximate N-Boc group was observed. In no case could allylic substitution be accomplished. From 13 compounds X-ray structure analyses could be obtained.

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Chiral Catalysts,
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The dipole moment (mu = 2.37 D), refraction (R = 106.71 cm3 ), and molar Kerr constant (mK x 1012 = -97.4) of 2,2′-diamino-1,1′-binaphtyl have been determined in benzene at 25.0 deg and lambda = 6328 Amstroem.The Kerr constant was measured by a relative method on apparatus with a special device for the preparation of solutions.The principal polarisabilities of the molecule (b1 = 36.05, b2 = 40.36, and b3 = 37.64 Amstroem3) shown that the ellipsoid of polarisability is somewhat extended in the direction of the 1,1′-bond.It is show that the naphthalene nuclei in the molecule are rotated about the 1,1′-bond by an angle phi cca 94 deg, i.e. the planes of the naphthalene rings are approximately perpendicular.94 degC, i.e. the planes of the naphthalene rings are approximately perpendicular.

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An oxidative skeletal rearrangement of 1,1?-binaphthalene-2,2?- diamines (BINAMs) that involves the cleavage of a strong C-C single bond of the binaphthalene unit and the nitrogen migration has been discovered. The unprecedented rearrangement enables access to a series of U-shaped azaacenes otherwise difficult to prepare in a selective manner by classical methods. Moreover, physicochemical properties of the unique azaacenes have been comprehensively investigated. This journal is the Partner Organisations 2014.

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Chiral Catalysts,
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A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 4488-22-6, Name is [1,1′-Binaphthalene]-2,2′-diamine, molecular formula is C20H16N2. In a Article,once mentioned of 4488-22-6, Safety of [1,1′-Binaphthalene]-2,2′-diamine

Absorption and vibrational circular dichroism (VCD) spectra of six 1,1?-binaphthyl derivatives were measured and analyzed on the basis of ab initio modeling. The spectra of both enantiomers were recorded with a high signal-to-noise ratio. The BPW91/6-31G** density functional theory level and the gauge invariant atomic orbitals were used for the simulations of VCD intensities. The binaphthyl moiety behaves as a chiral chromophore with a strong VCD signal because the 1,1?-substitution hinders its rotation. Most of the VCD bands were assigned, and the contributions of the binaphthyl skeleton and the functional groups could be clearly distinguished. Distinct VCD characteristics were found for the compounds exhibiting C2 and C1 symmetry. A very good agreement between the calculated and experimental spectra was observed. Apart from indication of enantiomeric purity, the spectra contain readable information about molecular conformation. The dihedral angle between the naphthyls planes, equal to about 55 when naphthyl residues were connected with PO4 covalent bridge, was found close to 90 for all the other derivatives.

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare

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Children learn through play, and they learn more than adults might expect. Science experiments are a great way to spark their curiosity, get their minds active, and encourage them to do something that doesn’t involve a screen. 4488-22-6, C20H16N2. A document type is Article, introducing its new discovery., category: chiral-catalyst

A highly efficient strategy for the kinetic resolution of axially chiral BINAM derivatives involving a chiral Bronsted acid-catalyzed imine formation and transfer hydrogenation cascade process was developed. The kinetic resolution provides a convenient route to chiral BINAM derivatives in high yields with excellent enantioselectivities. Chiral BINAMs on demand: A highly efficient strategy for the kinetic resolution of axially chiral BINAM derivatives involving a chiral Bronsted acid catalyzed imine formation and transfer hydrogenation cascade process was developed. The kinetic resolution provides a convenient route to chiral BINAM derivatives in high yields with excellent enantioselectivities.

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Chiral Catalysts,
Chiral catalysts – SlideShare

Extended knowledge of [1,1′-Binaphthalene]-2,2′-diamine

The reactant in an enzyme-catalyzed reaction is called a substrate. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction.I hope my blog about 4488-22-6 is helpful to your research., SDS of cas: 4488-22-6

The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.4488-22-6, Name is [1,1′-Binaphthalene]-2,2′-diamine, molecular formula is C20H16N2. In a Article,once mentioned of 4488-22-6, SDS of cas: 4488-22-6

A polyelectrolyte multilayer (PEM) coating consisting of the polypeptide, poly(L-lysine) hydrobromide, poly(L-lysine) and the polymeric dipeptide surfactant, poly(sodium undecanoyl-L-leutcyl-alaninate), poly(L-SULA), is investigated as a new medium for the separation of chiral analytes in open-tubular capillary electrochromatography (OT-CEC). In this approach, a stable PEM is constructed in situ by alternative rinses of the cationic polymer poly(L-lysine) and the anionic polymer poly(L-SULA). In previous studies, the PEM coating has been constructed by use of the cationic polyelectrolyte poly (diallydimethylammonium chloride), PDADMAC. In this study, we investigate the use of a biopolymer as the cationic polyelectrolyte. The results reported here indicate an increase in selectivity and resolution when poly(L-lysine) is used as the cationic polymer in place of PDADMAC. To evaluate the chromatographic performance of the PEM coating as a chiral stationary phase, the separation of the beta-blockers, labetalol and sotalol, and the binaphthyl derivatives, 1,1?-bi-2-naphthyl-2,2?-dihydrogen phosphate, 1,1?-bi-2- naphthol, and 1,1-binaphthyl-2,2?-diamine, are investigated. In addition, the effect of varying the amino acid order of the polymeric dipeptide surfactant on resolution is investigated. The number of bilayers also significantly influences the separation efficiency and resolution of enantiomers. The run-to-run and capillary-to-capillary reproducibilities are evaluated by calculating the relative standard deviations (RSDs) of the electroosmotic flow. These RSD values were found to be less than 1%. The coating is also stable and allows more than 290 runs to be performed in the same capillary. In addition, coupling of this chiral OT-CEC column with mass spectrometry is investigated.

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare