Category: 18531-94-7

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(Figure presented) Chiral macrocycles with the hydrogen bond donor/acceptor sites in the cavity were synthesized and covalently bonded to silica gel to give chiral stationary phases (CSPs), which showed excellent abilities to resolve various chiral compounds including ketones, esters, carboxylic acids, sulfoxides, amines, amino acid derivatives, and metal complexes. The effect of the linker connecting the macrocyclic moiety to silica was examined, and a more electronegative substituent was found to be better. Various organic solvents could be used as the mobile phase to optimize the resolution efficiency of the CSPs. Although the separation factors (alpha) tended to decrease with an increase in the solvent polarity, remarkable solvent tolerance was also observed. In some cases, even MeCN and MeOH could be used for the complete resolution of enantiomers. The MM calculations suggested that the chiral recognition of Co(acac)3 is achieved by a combination of steric interactions and hydrogen bonds between the carbonyl O atom coordinated to the Co atom and the macrocyclic amide NH groups. The attachment of substituents to the 3,3?-positions of the binaphthyl moiety improved chiral HPLC performance in some cases. In particular, CSP-1d, having the Br atoms, showed the best performance for several analytes.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Direct asymmetric reductive amination for the synthesis of (S)-rivastigmine

In this article we demonstrate how asymmetric total synthesis of (S)-rivastigmine has been achieved using direct asymmetric reductive amination as the key transformation in four steps. The route started with readily available and cheap m-hydroxyacetophenone, through esterification, asymmetric reductive amination, N-diphenylmethyl deprotection and reductive amination, to provide the final (S)-rivastigmine in 82% overall yield and 96% enantioselectivity. In the asymmetric reductive amination, catalysed by the iridium?phosphoramidite ligand complex and helped by some additives, the readily prepared 3-acetylphenyl ethyl(methyl)carbamate directly reductively coupled with diphenylmethanamine to yield the chiral amine product in 96% ee and 93% yield.

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, name: (R)-[1,1′-Binaphthalene]-2,2′-diol, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 18531-94-7, Name is (R)-[1,1′-Binaphthalene]-2,2′-diol, molecular formula is C20H14O2. In a Article, authors is Murai, Toshiaki，once mentioned of 18531-94-7

Fluorinative hydrolysis of phosphorothioic acid esters with a binaphthyl group through axis-to-center chirality transfer leading to the formation of P-chiral phosphorothioic monofluoridic acid salts

Asymmetric synthesis of P-chiral phosphorothioic monofluoridic acid ammonium salts was achieved via axis-to-center chirality transfer reactions by using phosphorothioic acid O-esters with a binaphthyl group, and the absolute stereochemistry of the salts was determined by X-ray analyses and by comparison of their CD spectra. This journal is

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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, name: (R)-[1,1′-Binaphthalene]-2,2′-diol, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 18531-94-7, Name is (R)-[1,1′-Binaphthalene]-2,2′-diol, molecular formula is C20H14O2. In a Article, authors is Mikhel, Igor S.£¬once mentioned of 18531-94-7

Synthesis, complexation behavior and application of a new diphosphite ligand in rhodium-catalyzed hydroformylation

Oxidative coupling of 3-(3-tert-butyl-4-hydroxyphenyl)propionic acid methyl ester (2) gave dimethyl 3,3?-(5,5?-di-tert-butyl-6,6?- dihydroxybiphenyl-3,3?-diyl)-dipropionate (1c), which upon phosphorylation/transesterification with a phosphochloridite derived from (R)-binaphthol, formed the new unsymmetrical binaphthol-bridged diphosphite 4. A rhodium catalyst based on 4 as ligand gave predominantly iso-selectivity in the hydroformylation of selected styrenes but opposite regioselectivity with 2,6-disubstituted derivatives. New chelate metal complexes (acac)RhL, PdCl 2L and PtCl2L have been synthesized by reacting 4 with (acac)Rh(CO)2, PdCl2(MeCN)2 and PtCl 2(COD), respectively. The structure of obtained compounds is determined based on 1H, 13C, 31P and 195Pt NMR spectroscopy and mass spectrometry data.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Synthesis and functionalization of hexacoordinate (Arenediolato)bis(polypyridyl)silicon(IV) Complexes

Hexacoordinate (arenediolato)silicon(IV) complexes that contain two additional 2,2?-bipyridine or 1,10-phenanthroline ligands are surprisingly stable against aqueous hydrolysis and therefore constitute attractive and novel templates for the design of bioactive compounds. In this article, we report the synthesis of (arenediolato)bis(polypyridyl)silicon(IV) complexes, including a case of diastereoselective synthesis of a nonracemic hexacoordinate (binaphtholato)silicon(IV) complex, and methods for their post-coordinative functionalization with halides, nitro, and carbonyl groups. Several X-ray crystal structures are provided and demonstrate the octahedral coordination of silicon in these complexes. Synthetic methods for the post-coordinative introduction of functional groups, namely, halides, nitro, and carbonyl groups, into hexacoordinate silicon(IV) complexes are reported that exploit the chemical robustness of (arenediolato)bis(polypyridyl)silicon(IV) complexes

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Metal-directed stereoselective syntheses of homochiral complexes of exo-bidentate binaphthol derivatives

The homochiral exo-bidentate ligands (S)-2,2?- bis(pyridylmethyleneoxy)-1,1?-binaphthyl [(S)-L] and (R)-2,2?- bis(pyridylmethyleneoxy)-1,1?-binaphthyl [(R)-L] were synthesized and employed for the preparation of coordination complexes with the aim of investigating the effect of an axially chiral 1,1?-binaphthyl connector on self-assembly process. Five homochiral complexes, [Ag{(S)-L}(ClO 4)]n (1), [Ag{(R)-L}(ClO4)]n (2), [{Cd{(S)-L}(H2O)Cl2}(H2O)0.5] n (3), [(Zn{(S)-L}Cl2)(DMF)0.5(H 2O)0.5]n (4), and [(Pd2{(S)-L} 2Cl4)(H2O)1.5]n (5), have been prepared and characterized by single-crystal X-ray diffraction analyses. The enantiomeric complexes 1 and 2 are isomorphous and are formed through interconnection of ligands and two-coordinate AgI centers. Complex 3 possesses a similar structural framework to 1 and is formed with two nitrogen atoms from (S)-L coordinating to six-coordinate CdII in a trans mode. The interlocking in part of the adjacent, one-dimensional helix-like chains stabilizes its structure. Complex 4 is a one-dimensional zigzag chain and is formed through interconnection of (S)-L and ZnCl2 units. The exo-bidentate (S)-L ligand in 5 links square-planar PdII into a homochiral dinuclear metallomacrocycle. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Preparation of enantiopure inherently chiral calix[5]arenes

Enantiopure inherently chiral calix[5]arenes were successfully prepared by separation of their (R)-BINOL diastereomeric derivatives of the corresponding racemates by column chromatography instead of HPLC. A new type of inherently chiral calix[5]arene was obtained.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Synthesis of a novel cage-functionalized chiral binaphthol host: A potential new agent for enantioselective recognition of chiral ammonium salts

Optically active, cage-functionalized crown ether (R)-3 which contains a 1,1′-bi-2-naphthol moiety has been prepared. Subsequently, the ability of (R)-3 to selectively recognize the enantiomers of guest ammonium salts, i.e., 4 and 5 in transport experiments was studied. Host (R)-3 displays significantly enhanced enantiomeric selectivity toward complex formation with 4 vis-a-vis complex formation with 5. The relative energetics of various relevant host-guest complexes have been investigated computationally. (C) 2000 Elsevier Science Ltd.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Reference of 18531-94-7, 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.18531-94-7, Name is (R)-[1,1′-Binaphthalene]-2,2′-diol, molecular formula is C20H14O2. In a article£¬once mentioned of 18531-94-7

Synthesis of TRIP and analysis of phosphate salt impurities

The chiral phosphoric acid TRIP, a useful Brnsted acid catalyst, easily becomes contaminated with metal impurities in the form of phosphate salts during synthesis. This significantly reduces the content of free acid in the product which can hamper the catalytic activity. Methods to easily judge whether TRIP contains mainly the free acid or phosphate salts are presented, using 1H NMR spectroscopy or a simple pH test. An improved synthetic protocol for TRIP was established that reliably produces the free acid.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Chemistry is traditionally divided into organic and inorganic chemistry. Computed Properties of C20H14O2. The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent£¬Which mentioned a new discovery about 18531-94-7

New chiral stationary phases based on xanthone derivatives for liquid chromatography

Six chiral derivatives of xanthones (CDXs) were covalently bonded to silica, yielding the corresponding xanthonic chiral stationary phases (XCSPs). The new XCSPs were packed into stainless-steel columns with 150 x 4.6 mm i.d. Moreover, the greening of the chromatographic analysis by reducing the internal diameter (150 x 2.1 mm i.d.) of the liquid chromatography (LC) columns was also investigated. The enantioselective capability of these phases was evaluated by LC using different chemical classes of chiral compounds, including several types of drugs. A library of CDXs was evaluated in order to explore the principle of reciprocity as well as the chiral self-recognition phenomenon. The separation of enantiomeric mixtures of CDXs was investigated under multimodal elution conditions. The XCSPs provided high specificity for the enantiomeric mixtures of CDXs evaluated mainly under normal-phase elution conditions. Furthermore, two XCSPs were prepared with both enantiomers of the same xanthonic selector in order to confirm the inversion order elution.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI