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Optical resolution method

The present invention provides three optical resolution methods. The first aspect comprises the steps of adding an optically active bifunctional resolving reagent to a bifunctional compound to form a liquid material, precipitating crystals therefrom, and treating the crystals and the liquid material separately with an acidic material, a basic material, or a basic material and an acidic material, to obtain a pair of enantiomers of an optically active bifunctional compound. The second aspect comprises an optical resolution method by which one necessary enantiomer of a pair of enantiomers in an optically active bifunctional compound is exclusively obtained. The third aspect comprises a method for racemizing one unnecessary enantiomer of a pair of enantiomers in an optically active bifunctional compound which is formed by the optical resolution method of the present invention.

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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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Opening of tartrate acetals using dialkylboron bromide: Evidence for stereoselectivity downstream from ring fission

Johnson-type acetals derived from dimethyl tartrate give, after opening with Me2BBr and cuprate displacement, secondary alcohols with high diastereoselectivity (>30:1). The mechanism proposed for the induction of diastereoselectivity is downstream from the ring fission. It implies a direct participation of the Lewis acid as a source of nucleophile and the stereospecific transformation of the resulting bromo acetal through an invertive and temperature-dependent process. The acetals are prepared by reaction of the desired aldehyde with dimethyl tartrate. Removal of the auxiliary is accomplished through Sml2 reduction or by an addition – elimination protocol using methoxide.

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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.Formula: C4H10O2. I hope my blog about 19132-06-0 is helpful to your research.

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Optical activity of vic-amino alcohols in the presence of dimolybdenum tetracetate

A straightforward and versatile method for the determination of the absolute configuration of vic-amino alcohols is proposed. The proposed method involves the in situ formation of chiral complexes of optically active ephedrine- or adrenaline-type vic-amino alcohols with the achiral dimolybdenum tetraacetate [Mo2(OAc)4] acting as an auxiliary chromophore. The resulting CD spectra are suitable for the assignment of absolute configuration, since the observed sign of Cotton effects arising within the d-d absorption bands for the metal cluster depends solely upon the chirality of the amino alcohol ligand. An empirically based rule correlating a positive/negative helicity expressed by the O-C-C-N torsional angle with the sign of Cotton effects occurring in the 400-260 nm spectral range has been formulated.

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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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Diastereomeric Right- and Left-Handed Helical Structures with Fourteen (R)-Chiral Centers

The relationship between chiral centers and the helical-screw control of their peptides has already been reported, but it has yet to be elucidated in detail. A chiral four-membered ring alpha,alpha-disubstituted alpha-amino acid with a (R,R)-butane-2,3-diol acetal moiety at the gamma-position, but no alpha-chiral carbon, was synthesized. X-ray crystallographic analysis unambiguously revealed that its homo-chiral heptapeptide formed right-handed (P) and left-handed (M) 310-helical structures at a ratio of 1:1. They appeared to be enantiomeric at the peptide backbone, but diastereomeric with fourteen (R)-configuration chiral centers. Conformational analyses of homopeptides in solution also indicated that diastereomeric (P) and (M) helices existed at approximately equal amounts, with a slight preference toward right-handedness, and they quickly interchanged at room temperature. The circumstances of chiral centers are important for the control of their helical-screw direction.

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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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A new twisted dual hydrogen bond acceptor featuring amidine functionality for chiral recognition: A high level of enantioselection of diol derivatives

The C2 amidine derivative (S,S)-1, as a twisted chiral dual acceptor for hydrogen bonding, was designed and synthesized. Enantioselective binding between (S,S)-1 and a series of diol enantiomers was investigated by NMR spectroscopy. High enantioselection above 1.0 kcal/mol was achieved in CDCl3. The association mode based on dual N¡¤¡¤¡¤HO interactions was confirmed by intermolecular NOEs.

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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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Mechanistic Studies of Diastereoselective Cyclopropanation via Homochiral Ketals. 1. Dioxolane Structural Effects

Compounds structurally related to 2-cyclohexen-1-one 1,4-di-O-benzyl-L-threitol ketal were prepared and subjected to the Simmons-Smith cyclopropanation.From these experiments a mechanistic model for diastereoselective cyclopropanation of common ring systems (five-, six-, and seven-membered) has been formulated.Diastereoselectivity is thought to result from preferential chelation of the Simmons-Smith reagent at the least sterically hindered lone pair of electrons on the dioxolane oxygen proximal to the alkene.It is found that the presence of oxygen atoms in the dioxolane appendages provide sites for competitive chelation of the reagent, which can antagonize the diastereoselection due to chelation at dioxolane oxygen.That chelation by dioxolane oxygen does occur and is responsible for diastereoselectivity is inferred from studies with a hydrocarbon model system.Surprisingly, both dioxolane appendages are shown to be necessary for optimum diastereoselection since, under the conditions of the Simmons-Smith cyclopropanation, 2-cycloalken-1-one ethylene ketals are reversibly ring opened to zwitterionic intermediates.

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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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SYNTHESE DIASTEREOSELECTIVE D’UNE COMPOSANTE DE LA PHEROMONE SEXSUELLE DE “L’ECAILLE ROUGE DE CALIFORNIE” : L’ACETATE D’ISOPROPENYL-6 METHYL-3 DECENE-9 YLE(3S, 6R)

6-Isopropenyl 3-methyl 9-decene yl acetate (3S, 6R) has been synthesized from readily available trans(-)-dihydrocarvone.Regioselective ozonolysis of this ketone silyl enol ether is the key step of the sequence and allows to preserve both chiral centers.

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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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Structural, spectroscopic, and computational characterization of the cleavage product of dimolybdenum(II) core under aerobic conditions

Full characterization of the adduct isolated in crystalline form from a solution of tetrakis(mu-trifluoroacetato) dimolybdenum(II) and (2S,3S)-butane-2,3-diol is reported herein. For this purpose X-ray crystallographic, spectroscopic, and computational methods were conducted. The single crystal X-ray diffraction analysis clearly indicates the cleavage of the MoMo quadruple bond in the chiral complex initially formed in situ after mixing the components. Cleavage product 2 shows two coordinated, symmetrically unequivalent (2S,3S)-butane-2,3-diol ligands associated with one Mo atom with different MoO bond lengths and MoOC bond angles. This inequivalence most likely reflects the engagement of the coordinated butanediol ligands in an intermolecular hydrogen bonding interaction with solvating butanediol molecules leading to the formation of an infinite helical chain pattern. Density functional theory (DFT) and time-dependent DFT calculations were used to provide support for the proposed structural assignment of 2 in acetonitrile and chloroform solutions, which were made on the basis of experimental CD and NMR results. Additional studies under anaerobic conditions have shown that the cleavage of the quadruple MoMo bond takes place only under aerobic conditions. Thus, it has been demonstrated that the changes in the shapes of the ECD curves observed over time are associated with spontaneous, air-oxidative cleavage of the quadruple MoMo bond and conversion of the Mo(II) to Mo(VI) centers.

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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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Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

Synthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is described. The stereochemical and synthetic features of this transformation are discussed in detail. In most instances, the nucleophile replaces the chloro substituent with retention of stereochemistry. With the oxygen nucleophiles, a second addition can occur leading to acetals, while with the nitrogen nucleophiles, E-Z isomerism occurs in the resulting enamine derivatives. The ratio of the E/Z isomers can be rationalised on the basis of the substituent and the level of 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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Chirality driven metallic versus semiconducting behavior in a complete series of radical cation salts based on dimethyl-ethylenedithio- tetrathiafulvalene (DM-EDT-TTF)

Enantiopure (S,S) and (R,R) dimethyl-ethylenedithio-tetrathiafulvalene (DM-EDT-TTF) 1 donors are synthesized by cross coupling followed by decarboxylation reactions. In the solid state the methyl groups are arranged in axial positions within sofa-type conformation for the six-membered rings. Crystalline radical cation salts formulated as [(S,S)-1]2PF 6, [(R,R)-1]2PF6, and [(rac)-1] 2PF6 are obtained by electrocrystallization. When the experiment is conducted with enantioenriched mixtures both enantiopure and racemic phases are obtained. The monoclinic enantiopure salts, containing four independent donors in the unit cell, show semiconducting behavior supported by band structure calculations of extended Hueckel type. The racemic salt contains only one independent donor in the mixed valence oxidation state +0.5. Under ambient pressure the racemic material is metallic down to 120 K, while an applied pressure of 11.5 kbar completely suppresses the metal-insulator transition. Band structure calculations yield an open Fermi surface, typical for a pseudo-one-dimensional metal, with unperfected nesting, thus ruling out the possibility of charge or spin density modulations to be at the origin of the transition. Raman spectroscopy measurements, in agreement with structural analysis at 100 K, show no indication of low-temperature charge ordering in the racemic material at ambient pressure, thus suggesting Mott-type charge localization for the observed metal-insulator transition.

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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