Awesome Chemistry Experiments For (S)-[1,1′-Binaphthalene]-2,2′-diol

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A series of optically active macrocyclic and acyclic bisbinaphthyls have been synthesized and characterized. The structure of one of the bisbinaphthyl macrocycles has been established by a single-crystal X-ray analysis. The UV and fluorescence spectra of these chiral compounds in various solvents and at different concentrations are studied. Formation of excimers is observed for the macrocyclic bisbinaphthyl compounds. Introduction of conjugated substituents to the 6,6?-positions of the binaphthyl units in the macrocycles leads to greatly amplified fluorescence signals. Using the 6,6?-substituted bisbinaphthyl macrocycles in place of the unsubstituted macrocycles allows a 2 orders of magnitude reduction in the sensor concentration for the fluorescence measurements. These macrocycles have exhibited highly enantioselective fluorescent enhancements in the presence of chiral alpha-hydroxycarboxylic acids and N-protected alpha-amino acids. They are useful as fluorescent sensors for chiral recognition. The macrocycles show much greater enantioselectivity in the substrate recognition than their acyclic analogues.

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Aryl addition reactions of ArTi(O-i-Pr)3 to aromatic, heteroaromatic, or alpha,beta-unsaturated ketones are described, producing tertiary alcohols in good to excellent enantioselectivities of up to 97% ee. The structure of the dititanium complex [(i-PrO)2Ti{mu-(S)-BINOLate} (mu-O-i-Pr)TiPh(O-i-Pr)2] [(S)-4] that simultaneously bears a chiral directing ligand and a nucleophile is reported. Complex (S)-4 possesses a pocket structure and has been illustrated as the key active species for addition reactions of both aldehydes and ketones. Mechanistic and stereochemical insights concerning addition reactions of organometallic reagents to organic carbonyls are rationalized based on the pocket structure and pocket size of (S)-4. Copyright

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We report on a new class of P-O monophosphite ligands (designated 3a-k) with a double six-membered-ring backbone onto which are attached additional groups and on applications of their Rh complexes in the hydrogenation of enamides, alpha-dehydroamino acid esters, dimethyl itaconate, and beta-(acylamino)acrylates. Our results demonstrate that the Rh complexes with ligands 3a-k exhibit high enantioselectivity and reactivity in asymmetric hydrogenation reactions. An ee value of up to 98.0% was obtained for the hydrogenation of alpha-dehydroamino acid esters, and the ee values were all over 99% for the other three types of substrate, with a turnover number of up to 5000.

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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 18531-99-2 is helpful to your research. Computed Properties of 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, 18531-99-2, name is (S)-[1,1′-Binaphthalene]-2,2′-diol, introducing its new discovery. Computed Properties of C20H14O2

(S)-1,1?-Binaphthyl-2,2?-diol was prepared in high optical purity (?98%) via Arthrobacter sp. lipase (MTCC No. 5125) catalyzed kinetic resolution. The immobilization of the substrate on a solid inert support significantly improved the enantioselectivity factor (E) by almost sixfolds, i.e. from ?27 to >180. The effect of acyl substituents and co-solvents were also studied.

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Excellent enantioselectivities are observed in palladium-catalyzed allylic substitutions of a wide range of substrate types and nucleophiles using a bidentate ligand composed of oxazoline and chirally flexible biaryl phosphite elements. This unusually wide substrate scope is shown by experimental and theoretical studies of its eta3-allyl and eta2-olefin complexes not to be a result of configurational interconversion of the biaryl unit, since the ligand in all reactions adopts an Sa,S configuration on coordination to palladium, but rather the ability of the ligand to adapt the size of the substrate-binding pocket to the reacting substrate. This ability also serves as an explanation to its excellent performance in other types of catalytic processes.

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 18531-99-2, molcular formula is C20H14O2, introducing its new discovery. Formula: C20H14O2

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,
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Described are bis(perfluoro-n-alkane-sulfonate) compounds, methods for preparing these compounds and use of these compounds, for example as starting materials for the synthesis of chiral and phosphine ligands for transition metal catalysts.

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The first complex of triphenylphosphine oxide (Ph3PO) with a chiral substrate, formed by crystallising Ph3PO in the presence of the synthetically important chiral auxiliary S-(-)-1,1?-bi-2,2?- naphthol (BINOL) is reported. The corresponding racemate form has also been prepared and the single-crystal X-ray diffraction structures of both reveal 1(BINOL):2(TPPO) stoichiometry. In the homochiral complex the TPPO molecules apparently exist in one enantiomeric form only. Crystal packing in both is dominated by intermolecular hydrogen bonding between a BINOL hydroxyl group and a TPPO oxygen atom (around 21 and 31 axes in the racemate and the chiral forms respectively). The crystalline racemate – a racemic compound rather than a conglomerate – is more densely packed than the homochiral form, thus apparently conforming to Wallach’s rule.

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 18531-99-2, molcular formula is C20H14O2, introducing its new discovery. name: (S)-[1,1′-Binaphthalene]-2,2′-diol

Novel hexacoordinated phosphate anions consisting of a central phosphorus(v) atom and at least one tetrachloropyrocatechol ligand can be simply prepared in modest to decent yields (37-71%) as their dimethylammonium salts following a one-pot process and with simple, usually commercially available, starting materials. A variety of symmetrical diones (alpha-diketones or ortho-quinones) can be used in this protocol and the structurally-diverse products are chemically stable when two tetrachloropyrocatechol ligands surround the P atom. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

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The optically pure monophosphites P(OAr)(BINOLate) (7, where Ar = 2,4-di-tert-butylphenyl) have been prepared by treatment of PCl2(OAr) with R- or S-BINOL. Treatment of [PdCl2(NCMe)2] with 7 gave [PdCl2(7)2] (9) or the binuclear orthometallated complex [Pd2Cl2(7-H)2] (8) depending on the reaction conditions. Bridge cleavage reactions of 8 gave [PdCl(7-H)(L)] with L trans to carbon when L = PPh3 or 7 and cis to carbon when L = N-heterocyclic carbene. Treatment of [PtCl2(NCtBu) 2] with 7 gave [PtCl2(7)2] (18) which upon further reaction with PtCl2 furnished a mixture of binuclear [Pt 2Cl2(7-H)2] (17) and cis-[PtCl(7-H)(7)] (19). The palladium complexes containing cyclometallated 7 were screened for catalysis of 1,4-conjugate addition of phenylboronic acid to cyclohexen-2-one and the allylation of benzaldehyde with allyltributyltin. Conversions were generally high in each case but enantioselectivities were low (15% e.e. at best). The X-ray crystal structures of 8, 17 and [PdCl(7-H)(NHC)] (10a, where NHC = 1,3-(dimesityl)imidazolidin-2-ylidene) have been determined.

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Metal catalyst and ligand design,
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