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Photoinversion of cisoid/transoid binaphthyls

Axially chiral binaphthyl-azobenzene cyclic dyads in which the two moieties are connected by two linkers of different lengths were synthesized. In the case of benzylated-binaphthyl analogue 2b, photoirradiation resulted in a dramatic change of the CD spectrum and optical rotation. Experimental and theoretical analyses indicated that the dihedral angle of the two naphthalene rings is strongly coupled to the azobenzene photoisomerization; cis-azobenzene induces a transoid-binaphthyl structure, while trans-azobenzene induces a cisoid-binaphthyl structure.

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Metal catalyst and ligand design,
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Preparation of optically active n-butyl(methyl)phenyl-, tert- butyl(methyl)phenyl- and isopropyl(methyl)phenylsilanes from the corresponding silyl chlorides using 2,2′-dihydroxy-1,1′-binaphthyls as resolving agents

Enantiomeric silanes 4a, 4b and 4c were obtained from the corresponding racemic silyl chlorides via diastereomeric derivatives with (R)- [1,1′]binaphthalenyl-2,2′-diol; the optical purity of silanes 4a and 4c was determined (> 98% ee) by HPLC using a chiral cyclodextrin-based column.

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Metal catalyst and ligand design,
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Enantioselective synthesis and stereoselective ring opening of N-acylaziridines

Kinetic resolution of N-acylaziridines by nucleophilic ring opening was achieved with (R)-BINOL as the chiral modifier under boron-catalyzed conditions (see scheme; Ar=3,5-dinitrophenyl). The consumed enantiomer of aziridine can be further converted to an enantioenriched 1,2-chloroamide with recovery of (R)-BINOL. Copyright

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

The important role of (R)-[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 18531-94-7, help many people in the next few years.Computed Properties of C20H14O2

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Chiral porphyrin dimer with a macrocyclic cavity for intercalation of aromatic guests

Chiral diporphyrin receptor 1, which has a macrocyclic cavity to sandwich aromatic guest molecules via double pi-pi stacking interactions, enabled the naked-eye detection of an aromatic explosive as well as chiral discrimination in NMR.

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

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The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 18531-94-7 is helpful to your research. HPLC of Formula: C20H14O2

In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 18531-94-7, name is (R)-[1,1′-Binaphthalene]-2,2′-diol, introducing its new discovery. HPLC of Formula: C20H14O2

HPLC enantioseparation with cellulose tris(3,5-dichlorophenylcarbamate) in aqueous methanol as a mobile phase

The appropriate design of mobile and stationary phase combinations allowed the use of cellulose tris(3,5-dichlorophenylcarbamate) (CDCPC) as the chiral stationary phase (CSP) in high-performance liquid chromatography (HPLC). Together with previous data obtained in n-hexane/2-propanol as a mobile phase the present study indicates very high chiral resolving ability of CDCPC.

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

Discovery of (R)-[1,1′-Binaphthalene]-2,2′-diol

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PROCESS FOR PRODUCTION OF DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALYST, PROCESS FOR PRODUCTION OF -AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE SALT

Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1′-binaphthyl-2,2′-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80C for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1′-binaphthyl-2,2′-disulfonate. The (R)-1,1′-binaphthyl-2,2′-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH2Cl2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0C for 30 minutes. A corresponding beta-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.

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

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Asymmetric Hydroformylation of Heterocyclic Olefins Mediated by Supramolecularly Regulated Rhodium-Bisphosphite Complexes

Rhodium complexes derived from conformationally transformable alpha,omega-bisphosphite ligands combined with a suitable alkali metal BArF salt as a regulation agent (RA) provide high regio- and enantioselectivities in the asymmetric hydroformylation (AHF) of three heterocyclic olefins. The outcome of the AHF could be exquisitely regulated by choosing the appropriate RA with an increase in the ee, the reversal of the regioselectivity, or the complete suppression of one byproduct.

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

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Chiral Anion Directed Asymmetric Carbocation-Catalyzed Diels-Alder Reactions

In recent years the carbocation has re-emerged as a highly efficient Lewis acid catalyst for a variety of organic transformations. However, the goal of asymmetric carbocation catalysis has so far been out of reach mainly as a result of difficulties associated with the preparation of stable chiral carbocations. Here, we describe developments towards asymmetric carbocation catalysis based on the concept of chiral-anion-directed catalysis. Chiral tritylium salts can be conveniently prepared in situ by mixing trityl chloride derivatives with chiral phosphonate, phosphoramide, bis(sulfonyl)amide, and bis(sulfuryl)amide silver or sodium salts. It is shown that the bis(sulfuryl)amide/tritylium ion salt catalyzes the Diels-Alder reaction with an up to 53 % enantiomeric excess. The enantioenriched triphenylmethylium/bis(sulfuryl)amide contact ion pair was applied in asymmetric counter-anion-directed catalysis to give Diels-Alder reaction adducts with up to 53 % ee.

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

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Synthesis of chiral 3,3?-disubstituted 1,1?-binaphthyl-2, 2?-disulfonic acids

A convenient synthesis of chiral 3,3?-disubstituted 1,1?-binaphthyl-2,2?-disulfonic acids (BINSA, 1) was developed. The key was directed ortho-lithiation of BINSA methyl ester 2 with n-BuLi and subsequent reaction with an electrophile. Electrophiles such as Br2, I2, Me3SiOTf, and i-PrOB(Pin) reacted smoothly with 3,3?-dilithiated BINSA methyl ester, and the corresponding 3,3?-dihalo-, 3,3?-bis(trimethylsilyl)-, and 3,3?-diboryl- BINSA derivatives were obtained in yields of 21-78%. This simple synthetic method is highly attractive since the ability to prepare 3,3?- disubstituted BINOLs in advance can be useful.

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Metal catalyst and ligand design,
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Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols

(Aqua)ruthenium(salen) complex 1c achieved good to high chemo- A nd enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce C1-symmetric bis(arenol)s from the combination of C3- A nd C7-substituted 2-naphthols or phenols even when there is no significant difference in oxidation potential between the cross-coupling partners. This unique cross-selectivity is dominated by steric rather than electronic effects of the arenols and can be controlled by chemoselective single-electron oxidation and oxidative carbon-carbon bond formation.

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