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Chiral binaphthyl-linked BODIPY analogues: Synthesis and spectroscopic properties

A chiral binaphthyl linked at the periphery and boron atom to form chiral BODIPY analogues has been prepared and characterized by various spectroscopies including single-crystal X-ray diffraction, 1H NMR, electronic absorption and CD, as well as fluorescence. Their chiroptical properties are dependent on the position of the chiral substituent. Attachment of a chiral binaphthyl group at the periphery to form (R)/(S)-2 displays positive and negative CD curves in the 260-400 nm region, and a chiral binaphthyl linked at the boron atom to form (R)/(S)-4 exhibits a negative/positive and positive/negative sign pattern in ascending energy terms in the main absorption spectra, respectively. Very low fluorescence quantum yields and solvent-dependent fluorescent bands for 2 are observed due to the excited-state intramolecular charge transfer. In the case of 4, the fluorescence is totally quenched, which can be attributed to the complete charge localization and negligible orbital overlap of the frontier MOs. TDDFT calculations reproduce experimentally observed spectroscopic data, and provide further insight into the nature of the electronic transitions.

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

Properties and Exciting Facts About (S)-[1,1′-Binaphthalene]-2,2′-diol

Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. I hope my blog about is helpful to your research. COA of Formula: C20H14O2

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Synthesis and optical resolution of a series of inherently chiral calix[4]crowns with cone and partial cone conformations

A series of inherently chiral calix[4]arenes with cone and partial cone conformations and with crown ether moieties of variable size have been readily synthesized. By taking advantage of the carboxy appendage on the lower rim, these were condensed with the chiral auxiliary (S)-BINOL to form diastereomers which, in most cases, could be separated by preparative TLC, or more desirably, by column chromato’graphy on silica gel (diaster-eomeric excess > 99% based on HPLC analysis). Seven enantiopure antipodes of inherently chiral calix[4]crowns were obtained after hydrolysis. It has been found that both the size of the crown moiety and alkylation of the last phenolic hydroxy group (accompanied with or without a change in the conformation) affect the separation of the diastereomers.

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

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Enantiomer separation of rac-2,2?-dihydroxy-1,1?-binaphthyl (BNO) by inclusion complexation with racemic or achiral ammonium salts and a novel transformation of a 1:1:1 racemic complex of BNO, Me4N +·Cl- and MeOH into a conglomerate complex in the solid state

The complete simultaneous and mutual enantiomer resolution of 2,2?-dihydroxy-1,1?-binaphthyl (BNO) and N-(3-chloro-2- hydroxypropyl)-N,N,N-trimethylammonium chloride, Me3N +CH2CH(OH)CH2Cl·Cl- into their enantiomers by inclusion complexation between their racemates in EtOH in the presence of a chiral seed crystal is reported. The enantiomer resolution of the rac-BNO was also accomplished easily by inclusion complexation with achiral ammonium salts, N-(2-hydroxyethyl)-N,N,N-trimethylammonium chloride, Me 3N+CH2CH2OH·Cl- and tetramethylammonium chloride, Me4N+·Cl -. Inclusion complexation of the rac-BNO with Me3N + CH2CH2OH·Cl- gave only a 1:1 conglomerate inclusion complex but not a racemic complex. Recrystallization of the rac-BNO and an equimolar amount of Me4N+· Cl- from MeOH (7 ml) and MeOH (15 ml) gave a 1:1:1 racemic complex, BNO·Me4N+·Cl-·MeOH and a 1:1 conglomerate complex, BNO·Me4N+·Cl -, respectively. Novel transformation of the former racemate into the latter conglomerate occurred by heating or by exposure to MeOH vapor in the solid state.

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

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Lipase-catalyzed stereoselective resolution and desymmetrization of binaphthols

We have investigated the use of lipoprotein lipase enzymes from Pseudomonas sp. and Pseudomonas fluorescens for the enantioselective resolution and desymmetrization of racemic binaphthols. The reactions were carried out using a non-aqueous environment (iPr2O/acetone/vinyl acetate), and yielded mono-acetate ester products of the parent unsubstituted substrate, the 6,6?-dibromo-substrate, and the 6,6?-dimethoxy-substrate with high enantiomeric selectivity.

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

New explortion of (S)-[1,1′-Binaphthalene]-2,2′-diol

I hope this article can help some friends in scientific research. I am very proud of our efforts over the past few months and hope to 18531-99-2, help many people in the next few years.Formula: C20H14O2

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, Formula: C20H14O2, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 18531-99-2, Name is (S)-[1,1′-Binaphthalene]-2,2′-diol, molecular formula is C20H14O2. In a Article, authors is Hamilton, James Y.,once mentioned of 18531-99-2

Iridium-catalyzed enantioselective allylic alkynylation

No leaving group needed: With an Ir(P,olefin) complex as catalyst, the direct enantioselective allylic alkynylation of secondary allylic alcohols with potassium alkynyltrifluoroborates as alkynylating reagents has been achieved. High levels of enantioselectivity and high yields were achieved with this operationally easy and robust protocol, the use of which was demonstrated in the synthesis of GPR40 receptor agonist AMG 837. cod=1,5-cyclooctadiene. Copyright

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

Properties and Exciting Facts About (S)-[1,1′-Binaphthalene]-2,2′-diol

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Enantioselective addition of diethylzinc to aldehydes using immobilized chiral BINOL-Ti complex on ordered mesoporous silicas

A chiral (S)-BINOL ligand has been covalently grafted on ordered mesoporous silicas-MCM-41 and SBA-15 and the resulting inorganic-organic hybrid materials used as chiral auxiliaries in Ti-promoted enantioselective addition of diethyl zinc to aldehydes under heterogeneous conditions. These heterogeneous catalysts showed promising activity and enantioselectivity. The catalyst having a larger pore diameter with capping of free silanol moiety with trimethylsilyl (TMS) group was found to be more active with enantioselectivities up to 81% being achieved. The catalyst worked well up to three cycles with retention of enantioselectivity after washing with 10% HCl in methanol.

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

Brief introduction of (S)-[1,1′-Binaphthalene]-2,2′-diol

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Homochiral 2,2?-bis(oxazolin-2-yl)- 1,1?-binaphthyl (boxax) ligands were anchored on various polymer supports including PS-PEG, PS, PEGA, and MeO-PEG via selective monofunctionalization at the 6-position of the binaphthyl backbone. Palladium(II) complexes of the supported boxax ligands catalyzed Wacker-type cyclization of 2-(2,3-dimethyl-2-butenyl)phenol to give 2-methyl-2-isopropenyl-2,3-dihydrobenzofuran with up to 96% ee.

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

Simple exploration of 18531-99-2

I hope this article can help some friends in scientific research. I am very proud of our efforts over the past few months and hope to 18531-99-2, help many people in the next few years.Computed Properties of C20H14O2

Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.In a patent, Computed Properties of C20H14O2, Which mentioned a new discovery about 18531-99-2

Silaborations of 1,3-cyclohexadiene and 1,3-cycloheptadiene were achieved using catalysts prepared from different combinations of phosphorus ligands and group 10 metal compounds. For the six-membered compound, 1,4-adducts with up to 82% ee were obtained employing Pt(0) and phosphoramidite ligands. For the seven-membered diene optimal conditions were found using catalysts based on Ni(0), but the highest selectivity observed was merely 22% ee. No improvement of the chiral induction was obtained using chiral silylboranes in combination with chiral phosphoramidite ligands in the additions to 1,3-cyclohexadiene. The adduct obtained from cyclohexadiene was used in allylborations of aldehydes under microwave irradiation to produce homoallylic alcohols with moderate to good diastereoselectivity.

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

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A new series of bipyridine based chiral organocatalysts for enantioselective Henry reaction

A series of binaphthol based chiral organocatalysts were synthesized and applied as metal-free organocatalysts in the enantioselective Henry reaction. These organocatalysts enabled the Henry reaction with a lower concentration of catalysts at room temperature affording the desired S- or undesired R-enantiomers. The formation of R- and S-enantiomers of beta-nitroalcohol products strongly depends on the temperature/substrate inversion of configuration for the effective catalytic enantioselective Henry reaction in high yields (up to 97%) with excellent enantioselectivities (up to 99% ee).

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

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Josiphos-Type Binaphane Ligands for Iridium-Catalyzed Enantioselective Hydrogenation of 1-Aryl-Substituted Dihydroisoquinolines

Convenient synthesis and useful application of a series of Josiphos-type binaphane ligands were described. The iridium complexes of these chiral diphosphines displayed excellent enantioselectivity and good reactivity in the asymmetric hydrogenation of challenging 1-aryl-substituted dihydroisoquinoline substrates (full conversions, up to >99% ee, 4000 TON). The use of 40% HBr (aqueous solution) as an additive dramatically improved the asymmetric induction of these catalysts. This transformation provided a highly efficient and enantioselective access to chiral 1-aryl-substituted tetrahydroisoquinolines, which were of great importance and common in natural products and biologically active molecules.

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