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Resolution of a racemic 1,2-diol using triphenylmethyl protection of the primary hydroxyl group and Mucor miehei lipase (Lipozyme) for the kinetic resolution

The triphenylmethyl group gives very simple access to the 1-protection of 1,2-diol as exemplified by racemic propane-1,2-diol. This group has, however, been shown to be incompatible with lipases commonly used for the resolution of alcohols. This turned out to be the case for Pseudomonas cepacia lipase, which we have used in our earlier work. Lipozyme, a Mucor miehei lipase, best known for 1,3-selectivity with glycerol is, however, shown to catalyze transacetylation onto the secondary hydroxyl group next to a triphenylmethoxy group. The transacetylation is completely enantioselective for the (R)-enantiomer giving a very simple method for the resolution of this type of 1,2-diol enantiomer.

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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

Properties and Exciting Facts About (2S,3S)-Butane-2,3-diol

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Sequential Kinetic Resolution of (+/-)-2,3-Butanediol in Organic Solvent Using Lipase From Pseudomonas cepacia.

Lipase from Pseudomonas capacia (PCL, Amano PS) catalyzed the enantioselective diacetylation of (+/-)-2,3-butanediol in vinyl acetate.Both acetylation steps favored the (R)-enantiomer (E1 = 12, E2 = 34), thus the reaction is a sequential kinetic resolution.The enantioselectivities of the two steps reinforced one another because both steps proceeded at comparable rates (S = 3) yielding an overall enantioselectivity of approximately 200.A synthetic-scale resolution starting from 2.7 g of (+/-)-2,3-butanediol yielded the diacetate ester of (R)-(-)-butanediol with 96percent ee (1.6 g, 30percent yield) and (S)-(+)-butanediol with 99percent ee (0.63 g, 23percentyield).This preparation is carried out entirely in organic solvent, thereby avoiding the difficult and low yield extraction of 2,3-butanediol from aqueous solution.

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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

Awesome Chemistry Experiments For (S)-Propane-1,2-diol

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PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE ALCOHOLS

A ruthenium complex RuCl[(S,S)-Tsdpen](p-cymene) represented by a formula below and a ketone compound are placed in a polar solvent, and the resulting mixture is mixed under pressurized hydrogen to hydrogenate the ketone compound and to thereby produce an optically active alcohol:

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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

Brief introduction of 1,5-Diphenylpenta-1,4-dien-3-one

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Studies on spiroheterocycles part-I: Installation of biologically active heterocyclic nuclei into spiro compounds derived from cyclohexanone and diphenyl thiobarbituric acid

Diarylidene ketones 1a-c, prepared by the condensation of acetone with different appropriate aldehydes, on Michael addition with 1,3-diphenyl- thiobarbituric acids afford the desired spiro compounds 2a-c. The diarylidene derivatives 3a-1 undergo cyclisation with hydrazine, phenyl hydrazine, hydroxylamine, urea and guanidine carbonate to furnish pyrazole 4a-1, phenyl pyrazole 5a-1, isoxazole 6a-1, pyrimidine 7a-1, and aminopyrimidine 8a-1 compounds, respectively. The structures of all the compounds have been confirmed on the basis of their analytical, IR, NMR and Mass spectral data. The antimicrobial activities of some of the compounds have also been reported.

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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

Can You Really Do Chemisty Experiments About 1,5-Diphenylpenta-1,4-dien-3-one

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Synthesis of new spiro-oxindolo-(pyrrolizidines/pyrrolidines) via cycloaddition reactions of azomethine ylides and dibenzylideneacetone

A comparative study of the synthesis of novel spiro-oxindolo(pyrrolizidine/ pyrrolidine) ring systems by the cycloaddition reaction of azomethine ylides generated by a decarboxylative route from sarcosine/proline and isatin with dibenzylideneacetone using various conditions is described. Graphical abstract: [Figure not available: see fulltext.]

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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

Properties and Exciting Facts About (S)-Butane-1,3-diol

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Design and synthesis of a novel class of dual PPARgamma/delta agonists

The design and synthesis of dual PPAR gamma/delta agonist (R)-3-{2-ethyl-4-[3-(4-ethyl-2-pyridin-2-yl-phenoxy)-butoxy]-phenyl}propionic acid is described. This compound dose-dependently lowered plasma glucose in hyperglycemic male Zucker diabetic fatty (ZDF) rats and produced less weight gain relative to rosiglitazone at an equivalent level of glucose control.

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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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Optically active macrocyclic cis-3 bis-adducts of C60: Regio- and stereoselective synthesis, exciton chirality coupling, and determination of the absolute configuration, and first observation of exciton coupling between fullerene chromophores in a chiral environment

A series of optically active cis-3 bis-adducts, such as (R.R.fC)-16 (Scheme 6), was obtained regio- and diastereoselectively by Bingel macrocyclization of C60 with bis-malonates, which contain optically active tethers derived from 1.2-diols. The absolute configuration of the inherently chiral addition pattern in cis-3 bis-adducts had previously been determined by comparison of calculated and experimental circular dichroism (CD) spectra. Full confirmation of these earlier assignments was now obtained by an independent method based on semiempirical AM1 (‘Austin Model 1’) and OM2 (‘Orthogonalization Method 2’) calculations combined with 1H-NMR spectroscopy. It was found computationally that bis-malonates [CHR(OCOCH2COOEt)]2, which contain (R.R)- or (S.S)-butane-2.3-diol derivatives as optically active tethers, preferentially form out-out cis-3 bis-adducts of C60 as a single diastereoisomer in which the alkyl groups R adopt a gauche conformation, while the two glycolic H-atoms are in an antiperiplanar (ap) and the ester linkages to the fullerene in a gauche relationship (Figs. 2 and 5). In contrast, in the less favorable diastereoisomer, which should not form, the alkyl groups R adopt an ap and the H-atoms a gauche conformation, while the ester bridges to the fullerene remain, for geometric reasons, locked in a gauche conformation. According to the OM2 calculations, the geometry of the fully staggered tether in the free bis-malonates closely resembles the conformation of the tether fragment in the bis-adducts formed. These computational predictions were confirmed experimentally by the measurement of the coupling constant between the vicinal glycolic H-atoms in the 1H-NMR spectrum. For (R,R,fC)-16, 3J(H,H) was determined as 7.9 Hz, in agreement with the ap conformation, and in combination with the calculations, this allowed assignment of the fC-configuration to the inherently chiral addition pattern. This conformational analysis was further supported by the regio- and diastereoselective synthesis of cis-3 bis-adducts from bis-malonates, including tethers derived from cyclic glycol units with a fixed gauche conformation of the alkyl residues R at the glycolic C-atoms. Thus, a bis-malonate of (R,R)-cyclohexane-1.2-diol provided exclusively cis-3 bis-adduct (R,R.fC)-20 in 32% yield (Scheme 7). Incorporation of a tether derived from methyl 4,6-O.O-benzylidene-a-D-glucopyranoside into the bis-malonate and Bingel macrocyclization diastereoselectively produced the cis-3 stereoisomer (a.D.fA)-22 (Scheme 8) as the only macrocyclic bis-adduct. If the geometry of the alkyl groups R at the glycolic C-atoms of the tether component deviates from a gauche relationship, as in the case of tethers derived from exo cis- and trans-norbornane-2.3-diol or from trans-cyclopentane-1.2-diol, hardly any macrocyclic product is formed (Schemes 5 and 9). The absolute configurations of the various optically active cis-3 bis-adducts were also assigned by comparison of their CD spectra, which are dominated by the chiroptical contributions of the inherently chiral fullerene chromophore (Figs. 1, 3, and 4). A strong chiral exciton coupling was observed for optically active macrocyclic cis-3 bis-adducts of C60 with two appended 4-(dimethylamino)benzoate ((S.SfC)-26; Fig. 6) or meso-tetraphenylporphyrin ((R.R.fC)-28: Fig. 7) chromophores. Chiral exciton coupling between two fullerene chromophores was observed for the first time in the CD spectrum of the threitol-bridged bis-fullerene (R.R)-35 (Fig. 9).

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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

Final Thoughts on Chemistry for (S)-Propane-1,2-diol

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The Influence of Intramolecular Dynamics on Branching Ratios in Thermal Rearrangements

1- and 2-phenylbicyclo<2.1.1>hex-2-enes-5-d undergo thermal rearrangement to give products, differing only in the location of the deuterium, in ratio of about 9:1, but with identical activation enthalphies.Similarly, opticallly active trans-2-methyl-1-(trans-2-phenylethenyl)cyclopropane is found to rearrange to enantiomeric methylphenylcyclopentenes that are formed in a 5.9:1 ratio but with virtually identicyl activation enthalphies.Barring repeated coincidence, these results do not seem to be explicable within the framework of statistical theories of unimolecular kinetics such as RRKM theory, transition state theory, and variational transition state theory.The possible influence of dynamic effects in these and other unimolecular reactions is 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

Some scientific research about (2S,3S)-Butane-2,3-diol

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A New Chiral Rhodium(I) Complex of (2R,3R)-2,3-Bis(diphenylphosphino)butane for Asymmetric Hydrogenations

Rhodium(I) complexes of the new chiral ligand (2R,3R)-2,3-bis(diphenylphosphino)butane (4) – which is easily prepared from natural tartaric acid – hydrogenate alpha-(acylamino)acrylic acids to natural (S)-acylamino acids in high chemical (95-100percent) and optical (80-100percent) yields.

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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