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BORON FLUORIDE PROMOTED CLEAVAGE OF ACETALS BY ORGANOCOPPER REAGENTS. APPLICATION TO ASYMMETRIC SYNTHESIS

In the presence of BF3*Et2O, organocopper and cuprate reagents promote the substitution of one alkoxy group of an acetal.Under the same conditions, alkoxy tetrahydropyrans react selectively, by ring cleavage.Chiral cyclic acetals, having a C2 axis of symmetry are diastereoselectively cleaved.The method serves to synthesize chiral secondary alcohols, after the removal of the chiral auxiliary.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Sulfur-containing optically active polymers. iv asymmetric synthesis of optically active poly(gamma-ketosulfide)s by polyaddition of 1,3-dimercaptobenzene to alpha,beta,alpha’,beta’-unsaturated acyclic or cyclic ketones in the presence of (-)-cinchonidine

Optically active poly(y-ketosulfide)s can be obtained by polyaddition of 1,3-dimercaptobenzene to prochiral di-unsaturated ketones in the presence of (-)-cinchonidine as promoter of asymmetric induction. As proved with low molecular-weight model compounds, the enantiomeric excess found in the addition product is related to steric hindrance and conformational rigidity of the ketonic reagent as well as to reaction temperature, in accordance with the high sensitivity of this type of homogeneous catalysis to substrate structure and experimental conditions.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Archives for Chemistry Experiments of (S)-Propane-1,2-diol

COA of Formula: C3H8O2, Interested yet? Read on for other articles about COA of Formula: C3H8O2!

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A General Route to Enantiomerically Pure Sulfoxides from a Chiral Sulfite

Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate.This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselectivity (>90:10).Addition of a second organometallic transforms the purified sulfinate in excellent yield into a chiral sulfoxide (100percent ee) of predictable absolute configuration.The mechanism and scope of this approach are discussed.This method completes the various other methdos of preparation of chiral sulfoxides and is especially convenient for the preparation of tert-butyl sulfoxides.Examples for the synthesis of many chiral tert-butyl sulfoxides are given.The case of chiral sulfites derived from a C2 diol or of a chiral monoalcohol is also proposed as a route to chiral sulfinates, and some promising preliminary results have been obtained.The general main route to obtain chiral sulfoxides from sulfites are also discussed.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Volatile composition of Baga red wine: Assessment of the identification of the would-be impact odourants

Wines produced from Baga native variety from the Portuguese Bairrada Appellation, harvest 2000, were submitted to a liquid-liquid continuous extraction with dichloromethane and analysis by gas chromatography-mass spectrometry (GC-MS). A total of 53 compounds were identified and quantified. This wine has 225 mg l-1 volatile compounds, which include aliphatic and aromatic alcohols (44%), acids (27%), esters (15%), lactones (6%), amides (5%), and phenols (1%). To achieve the identification of the major would-be impact odourants, the aroma index was calculated using the concentration of each volatile component and the corresponding odour threshold reported in the literature. This methodology proved suitable, as a preliminary step, for the determination of the would-be impact odourants of Baga wine. From the 53 compounds identified, nine were determined as the most powerful odourants: guaiacol, 3-methylbutanoic acid, 4-ethoxycarbonyl-gamma-butyrolactone, isobutyric acid, 2-phenylethanol, gamma-nonalactone, octanoic acid, ethyl octanoate and 4-(1-hydroxyethyl)-gamma-butyrolactone. These data suggest Baga wine as a fruity-type product with an aroma correlated to a restricted number of compounds.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Asymmetric hydrogenation of alpha-hydroxy ketones catalyzed by MsDPEN-Cp*Ir(III) complex

Asymmetric hydrogenation of a series of alpha-hydroxy aromatic ketones in methanol catalyzed by Cp*Ir(OTf)(MsDPEN) (MsDPEN = N-(methanesulfonyl)-1, 2-diphenylethylenediamine) affords the 1-aryl-1,2-ethanediols in up to 99% ee. The reaction can be conducted with a substrate-to-catalyst molar ratio at high as 6000 under 10 atm of H2-1-Hydroxy-2-propanone is also hydrogenated with high enantioselectivity.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Purification and characterization of membrane-bound quinoprotein cyclic alcohol dehydrogenase from Gluconobacter frateurii CHM 9.

A quinoprotein catalyzing oxidation of cyclic alcohols was found in the membrane fraction for the first time, after extensive screening among aerobic bacteria. Gluconobacter frateurii CHM 9 was finally selected in this study. The enzyme tentatively named membrane-bound cyclic alcohol dehydrogenase (MCAD) was found to occur specifically in the membrane fraction, and pyrroloquinoline quinone (PQQ) was functional as the primary coenzyme in the enzyme activity. MCAD catalyzed only oxidation reaction of cyclic alcohols irreversibly to corresponding ketones. Unlike already known cytosolic NAD(P)H-dependent alcohol-aldehyde or alcohol-ketone oxidoreductases, MCAD was unable to catalyze the reverse reaction of cyclic ketones or aldehydes to cyclic alcohols. MCAD was solubilized and purified from the membrane fraction of the organism to homogeneity. Differential solubilization to eliminate the predominant quinoprotein alcohol dehydrogenase (ADH), and the subsequent two steps of column chromatographies, brought MCAD to homogeneity. Purified MCAD had a molecular mass of 83 kDa by SDS-PAGE. Substrate specificity showed that MCAD was an enzyme oxidizing a wide variety of cyclic alcohols. Some minor enzyme activity was found with aliphatic secondary alcohols and sugar alcohols, but not primary alcohols, differentiating MCAD from quinoprotein ADH. NAD-dependent cytosolic cyclic alcohol dehydrogenase (CCAD) in the same organism was crystallized and its catalytic and physicochemical properties were characterized. Judging from the catalytic properties of CCAD, it was apparent that CCAD was distinct from MCAD in many respects and seemed to make no contributions to cyclic alcohol oxidation.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.category: chiral-oxygen-ligands. I hope my blog about 19132-06-0 is helpful to your research.

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, category: chiral-oxygen-ligands, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. category: chiral-oxygen-ligands, Name is (2S,3S)-Butane-2,3-diol, molecular formula is C4H10O2. In a Article, authors is Aoki, Shin£¬once mentioned of category: chiral-oxygen-ligands

SIMPLE CHIRAL CROWN ETHERS COMPLEXED WITH POTASSIUM TERT-BUTOXIDE AS EFFICIENT CATALYSTS FOR ASYMMETRIC MICHAEL ADDITIONS

Simple C2-symmetric chiral crown ether 1 complexed with KOtBu was found to work as an efficient chiral catalyst in Michael additions to cause high asymmetric induction.The results with various chiral crown ethers as catalysts suggest that diaxial-like conformation of the vicinal methyl groups of 1<*>potassium enolate complex is responsible for the chiral induction.

The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.category: chiral-oxygen-ligands. I hope my blog about 19132-06-0 is helpful to your research.

Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Archives for Chemistry Experiments of (S)-Propane-1,2-diol

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Functional characterization of a stereospecific diol dehydrogenase, FucO, from Escherichia coli: Substrate specificity, pH dependence, kinetic isotope effects and influence of solvent viscosity

FucO, (S)-1,2-propanediol oxidoreductase, from Escherichia coli is involved in the anaerobic catabolic metabolism of l-fucose and l-rhamnose, catalyzing the interconversion of lactaldehyde to propanediol. The enzyme is specific for the S-enantiomers of the diol and aldehyde suggesting stereospecificity in catalysis. We have studied the enzyme kinetics of FucO with a spectrum of putative alcohol and aldehyde substrates to map the substrate specificity space. Additionally, for a more detailed analysis of the kinetic mechanism, pH dependence of catalysis, stereochemistry in hydride transfer, deuterium kinetic isotope effect of hydride transfer and effect of increasing solvent viscosity were also analyzed. The outcome of this study can be summarized as follows: FucO is highly stereospecific with the highest E-value measured to be 320 for the S-enantiomer of 1,2-propanediol. The enzyme is strictly regiospecific for oxidation of primary alcohols. The enzyme prefers short-chained (2-4 carbons) substrates and does not act on bulkier compounds such as phenyl-substituted alcohols. FucO is an ‘A-side’ dehydrogenase transferring the pro-R-hydrogen of NADH to the aldehyde substrate. The deuterium KIEs of kcat and k cat/KM were 1.9 and 4.2, respectively, illustrating that hydride transfer is partially rate limiting but also that other reaction steps contribute to rate limitation of catalysis. Combining the KIE results with the observed effects of increasing medium viscosity proposed a working model for the kinetic mechanism involving slow, rate limiting, product release and on-pathway conformational changes in the enzyme-nucleotide complexes.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.Electric Literature of 19132-06-0. I hope my blog about 19132-06-0 is helpful to your research.

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Chemical Transformation of Terpenoids. VII. Syntheses of Chiral Segments, Key Building-Blocks for the Right Half of Taxane-Type Diterpenoids

Two kinds of chiral segments, i.e. segment B-I (4) and segment B-II (5), which are potentially versatile building-blocks for construction of the right half of taxane-type diterpenoids, were synthesized from 3-methyl-2-cyclohexen-1-one (6) via optical resolution of the (2S,3S)-2,3-butanediol ketal derivatives (8, 15).Keywords – taxane-type diterpenoid; optical resolution with (2S,3S)-2,3-butanediol ketal; CD of cyclopropyl ketone; HPLC for optical resolution; ?-allylpalladium complex.

The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.Electric Literature of 19132-06-0. I hope my blog about 19132-06-0 is helpful to your research.

Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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Preparation of enantiomerically pure 1,3-butanediol from threonine

Enantiomerically pure R or S 1,3-butanediols were prepared in four steps from L to D threonine by nitrous deamination in the presence of bromide ion followed by esterification and reduction.

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Reference£º
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate