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The enantioface-differentianing hydrogenation of 4-hydroxy-2-butanone (I) to 1,3-butanediol (II) was conduced with asymmetrically modified metal catalysts.Among the modified catalysts examined, Raney nickel modified with a solution containing tartaric acid and NaBr (TA-NaBr-MRNi) gave the best results with respect to the optical and chemical yields. (R)-II, an optical purity of 69 percent was obtained in a quantitative chemical yeld by the use of (R,R)-TA-NaBr-MRNi. (S)-II was also obtained by the use of (S,S)-TA-NaBr-MRNi.A simple method for the preparation of optically pure (S)- and (R)-II from the hydrogenation product was also developed.

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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 cis- and trans-2-methyl-2-oxo-2-trityl-1,3,2-dioxaphosphorinanes were obtained in the Arbuzov reaction of 2-methoxy-4-methyl-1,3,2-dioxaphosphorinane with trityl chloride. The NMR spectra (1H, 13C and 31P) in solution indicated that trans isomer exists in the form of two noncongruent molecules and it adopts two different conformations: a halfchair and a sofa, while the cis isomer exists as the mixed half/chair-sofa conformer. The compounds crystallise as a pure chiral forms and as a racemates. The solid state structural studies show that NMR data are consistent with the single crystal X-ray analysis, but the conformation existing in the crystal structure is more complex than it can be supposed on sole NMR determination. Crystal data: cis-isomer chiral form: space group P32, a = 8.782, b = 8.782, c = 21.680, alpha = 90.00, beta = 90.00, gamma = 120.00, V = 1448.0; cis-isomer racemate: space group Pca21, a = 16.773, b = 8.491, c = 27.006, alpha = 90.00, beta = 90.00, gamma = 90.00, V = 3846.2; trans-isomer racemate: space group Cc, a = 16.133, b = 8.388, c = 16.158, alpha = 90.00, beta = 117.20, gamma = 90.00, V = 1944.8; trans-isomer chiral form: space group P 1, a = 8.397, b = 9.003, c = 14.944, alpha = 80.76, beta = 74.38, gamma = 63.31, V = 971.1).

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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 acetal protected 4-amino-2-pentanone was synthesised by two different routes in 10 and seven steps, respectively, the key step being a microbiological reduction. Both enantiomers of the amine were obtained enantiomerically pure.

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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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Geotrichum sp. WF9101 could degrade (S)-(+)-1,2-propanediol, (S)-(+)- 1,3-butanediol, and (2S,4S)-(+)-2,4-pentanediol, but not the corresponding enantiomers. An NAD+-linked secondary alcohol dehydrogenase purified from the strain showed the same enantioselective oxidations towards these diols. This enzyme is proposed to be useful for the preparation of (R)-(-)-diols from the racemates of these diols.

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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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Complexes RuCl2(ArCN)2(binap), II (binap=(R)- or (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl; ArCN=benzonitrile, a; 2-furancarbonitrile, b; pentafluorobenzonitrile, c) were prepared, and their solution properties were investigated by 31P NMR measurements.The catalytic aactivities and enantioselectivities for IIa-c catalysed hydrogenation of some prochiral acids were very similar to those provided by Ru2Cl4(binap)2(NEt3), I.In the hydrogenation of beta-functionalized carbonyl compounds, however, IIa-c showed considerably lower activities and/or selectivities, compared with complex I.The differences in IIa-c catalysed reactions are discussed in relation to the coordinating abilities of ArCN in II.

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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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(S)-2-Methyloxetane (1) and its precursor (S)-1,3-butanediol (2) were prepared in low to moderate chemical yield with less than 0.5percent racemization from (S)-ethyl lactate (4) and from (2S,3S)-allothreonine (14b).For the first time the enantiomeric purities of both the starting material and the product (1) were carefully determined by high-precision capillary gas chromatography on optically active resolving stationary phases.The validity of the quadrant rule, correlating the relative configuration of alkyloxiranes with the order of elution from manganese(II) bis<(1R)-3-(heptafluorobutyryl)camphorate> (3) by complexation gas chromatography, is also confirmed for 2-methyloxetane (1).

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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 compound of Formula (I) as described herein or a pharmaceutically acceptable salt, solvate or ester thereof. The compounds are useful as inhibitors of the HDM2 protein. Also disclosed are pharmaceutical compositions comprising the above compounds and methods of treating cancer using the same.

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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 short and convergent synthesis of (5S)-HETE 1a was accomplished by coupling of two easily accessible synthons 2 and 3a.

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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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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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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