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Chiral and achiral allyltrichlorostannanes reacted with chiral beta-alkoxy and syn and anti alpha-methyl-beta-alkoxy aldehydes to give the corresponding homoallylic alcohols with moderate to high diastereoselectivities.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen’s hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Aliphatic ketones, e.g., butanone, are converted nearly quantitatively to the corresponding dioxolanes (ketals) in neat (S)- or (RS)-1,2-propanediol containing dichloroacetic acid.The reactions follow the pseudo-first-order law at a given acid concentration, are inhibited by water, and proceed approximately twofold faster in (RS)-diol-O,O-d2 than in undeuterated diol.No difference in rates greater than 1percent could be detected between (S)- and (RS)-diols at identical temperatures, acid concentrations, and water concentrations.Thus, for a chiral diol molecule and the activated complex, free-energy differences are virtually the same in (S)- and (RS)-diols as solvents.Differences in interactions among identical and enantiomeric molecules, if any, are evidently matched by differences in the activated complexes.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A catalyst consisting of polyaniline-anchored metal salts is used as a Lewis acid to promote the Michael reaction of ,-unsaturated ketones. The reaction is performed efficiently with imidazole, acetyl acetone, and ethyl acetate as Michel donors and chalcones as the acceptors under ultrasound irradiation.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Wavelength and mass resolved resonance-enhanced multiphoton ionization (REMPI) excitation spectra of (R)-(+)- 1-phenyl-1-propanol (PR) and its complexes with some chiral diols, i.e. 1,2-propanediols. 2.3-butanediols, and 2,4-pentanediols, have been recorded after a supersonic molecular beam expansion and interpreted in the light of molecular dynamic (MD) conformational minima searches. The spectral features of the selected complexes were found to depend on cooperative hydrogen-bond interactions between the two components, whose intensity depends upon the specific configuration of the diol moiety and the relative position of its hydroxy groups. The study further confirms resonant two-photon ionization spectroscopy, coupled with time-of-flight mass resolution (R2PI-TOF), as an excellent tool for gathering valuable information on the interactive forces in molecular clusters and for enantiodiscrimination of chiral molecules in the gas phase.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The present invention provides a process for producing an optically active fluoro compound represented by formula (3) through reaction between a specific fluoroamine and an optically active diol; and a process for producing an optically active fluoroalcohol through hydrolysis of the optically active fluoro compound. According to the process of the present invention, such optically active fluoro compounds and optically active fluoroalcohols can be produced at high optical purity and high yield in a simple manner. Such optically active fluoroalcohols are a useful source for producing drugs, pesticides, and other functional chemicals.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The detailed procedure for the synthesis of Ru-SYNPHOS and Ru-DIFLUORPHOS catalysts are described. These catalysts displayed high rates and are quite effective for the large-scale hydrogenation reactions of unsaturated compounds. Georg Thieme Verlag Stuttgart.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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N,N’-dimethyl-4,4′-azopyridinium methyl sulfate (MAZP) was characterized as an electron transfer mediator for oxidation reactions catalyzed by NAD+- and pyrroloquinoline quinone (PQQ)-dependent alcohol dehydrogenases. The bimolecular rate constant of NADH reactivity with MAZP was defined as (2.2 ± 0.1) × 105 M?1 s?1, whereas the bimolecular rate constant of reactivity of the reduced form of PQQ-dependent alcohol dehydrogenase with MAZP was determined to be (4.7 ± 0.1) × 104 M?1 s?1. The use of MAZP for the regeneration of the cofactors was investigated by applying the electrochemical oxidation of the mediator. The total turnover numbers of mediator MAZP and cofactor NADH for ethanol oxidation catalyzed by NAD+-dependent alcohol dehydrogenase depended on the concentration of the substrate and the duration of the electrolysis, and the yield of the reaction was limited by the enzyme inactivation and the electrochemical process. The PQQ-dependent alcohol dehydrogenase was more stable, and the turnover number of the enzyme reached a value of 2.3 × 103. In addition, oxidation of 1,2-propanediol catalyzed by the PQQ-dependent alcohol dehydrogenase proceeded enantioselectively to yield L-lactic acid.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A thiophene compound represented by formula (I): 1in which: A represents a C2-C5 alkylene bridge; R represents a stereoselectively substituted, linear or branched C2-C24 alkyl, C3-C18 cycloalkyl, C1-C18 alkoxy or polyethyleneoxide group, optionally substituted with at least one substituent selected from the group consisting of an alcohol, amide, ether, ester or sulfonate group; or an optionally substituted aryl group having at least one chiral centre substituted at said C2-C5 alkylene bridge; polymers derived therefrom; a process for polymerizing a thiophene according to formula (I), optionally chemically or electrochemically; and dispersions, pastes and layers containing polymers derived therefrom.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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An efficient, convergent approach for the total synthesis of aigialomycin D 1 is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hydroxy-bearing stereogenic centers at the C5? and C6? positions; (b) a Kocienski modified Julia protocol to construct the two E-configured double bonds; and (c) Yamaguchi macrolactonization to acccess the 14-membered macrocyclic ring.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate