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Asymmetric hydrosilylation of symmetrical diketones with diphenylsilane in the presence of catalytic amount (/ = 100> of rhodium complex coordinated with trans-chelating chiral phosphine ligand EtTRAP gave corresponding optically active symmetrical diols with high enantiomeric excesses.

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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 acetal of (2S,3S)-butane-2,3-diol and furfural is equilibrated in molten maleic anhydride with one major crystalline product which is a 1:1 complex of maleic anhydride and (1S,2R,3S,4R,4’S,5’S)-1-(4′,5′-dimethyldioxolan-2′-yl)-7-oxabicyclo[2. 2.1]hept-5-ene-2-exo,3-exo-dicarboxylic anhydride. This compound was converted into (1S,4R,4’S,5’S)-1-(4′,5′-dimethyldioxolan-2′-yl)-5,6-dimethylidene-7-o xabicyclo[2.2.1]hept-2-ene (+)-12, the circular dichroism spectrum of which suggests a slightly skew s-cis-butadiene chromophore as confirmed by X-ray diffraction. Copyright (C) Elsevier Science Ltd.

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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 reaction of gamma-silyl allylic alcohol and its ether with ozone provides synthetically versatile alpha-formyl silyl peroxide in good yield without normal fission of carbon-carbon double bond. Thus, the provided silyl peroxide serves as a good precursor for the stereochemically defined triol derivative via alkylation and reduction of peroxide moiety.

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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 sulfonic-acid-functionalized ionic liquid is used as a Bronsted acid catalyst for the efficient synthesis of indole derivatives in good-to-high yields at room temperature under solvent-free conditions. The catalyst can be reused for ten consecutive runs without significant loss of activity.

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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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Aryl- and hetarylpyrazolines smoothly undergo photoaromatization under irradiation with the visible light (lambda > 400 nm) in the presence of carbon tetrachloride. The reaction is accompanied by an increase in the acidity of the medium and a change in the fluorescence. The structure of pyrazoline and solvent considerably affect the photoaromatization rate. The mechanism of the reaction was proposed, which agrees with the experimental data.

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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 Michael addition reaction of differently substituted enones with carbon, sulfur, oxygen, and nitrogen nucleophiles has been achieved by a new heterobimetallic “Pd-Sn” catalyst system. The nature of the catalytically relevant species and their interactions with the enone moiety has been examined by spectroscopy. The effect of ligand and the coordination mode of enone with “Pd-Sn” heterobimetallic system have been investigated by kinetics and DFT studies. A straightforward application of this methodology is shown in the synthesis of 1,4-oxathiepane core.

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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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Spiroannulation has been achieved by double Michael reaction under very mild conditions using a phase transfer catalyst.Various cyclohexanone molecules having different steric requirements have been condensed with 1,5-diphenyl-1,4-pentadien-3-one in the presence of cetyltrimethylammonium bromide.This condensation reaction was found to be diastereospecific as well as regiospecific.Stereoisomers derived from homotopic cycloalkanones were found to adopt endo geometry, while diastereotopic cycloalkanones were found to elaborate a mixture of endo and exo diastereomers.These stereochemical inferences are drawn based on extensive 2D-nmr studies employing COSY and NOESY experiments.

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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

Discovery of (S)-Butane-1,3-diol

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Electric Literature of 24621-61-2. In my other articles, you can also check out more blogs about 24621-61-2

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Prostereogenic mono- and dicarbamates of 1,3-propanediol and 1,4-butanediol are deprotonated by the sec-butyllithium/(-)-sparteine system with high enantiotopic differentiation.The electrophilic substitution of the intermediate chiral carbanions furnishes the title compounds with >95percent ee. Key words: Chiral 1-oxy-carbanions; enantioselective deprotonation; (-)-sparteine.

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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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Herein we report the synthesis of gamma-keto-delta-alkenyl-phosphonates and phosphine oxides by two versions of strategy (a) which involves the addition of dialkyl phosphites to alpha,alpha?-diarylideneketones, and by strategy (b) which utilizes the reaction of P-chlorodiphenylphosphine with diarylidene ketones in acetic acid. On reaction with hydrazine derivatives, gamma-keto-delta-alkenyl-phosphonates and phosphine oxides give 3-phosphonoethylpyrazoline derivatives which can be converted into the corresponding aromatic pyrazoles by oxidative dehydrogenation, using sodium nitrite as oxidizing agent.

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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

Why Are Children Getting Addicted To (2S,3S)-Butane-2,3-diol

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Enantioselective epoxide hydrolysis by yeasts has been demonstrated for the hydrolysis of several aryl, alicyclic and aliphatic epoxides by a strain of Rhodotorula glutinis. High enantioselectivity was obtained in the hydrolysis of methyl substituted aryl and aliphatic epoxides whereas selectivity towards terminal epoxides in all cases was lower. Homochiral vicinal diols were formed from several methyl substituted epoxides and also from meso epoxides. Kinetic resolution of trans-1-phenyl-1,2-epoxypropane was studied in more detail.

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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