Category: 538-58-9

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The reaction of selenium monoketo ylides with the dibenzylidene derivatives of ketones (acetone, cyclopentanone, cyclohexanone) only takes place at one double bond of the dienone by a mechanism of the <1+2>-cycloaddition type with the formation of two isomeric cyclopropyl ketones.In the case of the dibenzylidene derivative of bicyclo<3.3.1>nonan-3-one the type of reaction, i.e., <1+2>– or <1+4>-cycloaddition, is determined by the direction of attack by the selenonium ylide (axial or equatorial).

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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 Dess-Martin Periodinane (DMP) [1,1,1-triacetoxy-1,1-dihydro-1,2- benziodoxol-3(1H)-one], oxidatively deoximates aldoximes as well as ketoximes in very high yields, smoothly in short time, and under mild conditions. Deoximation occurs selectively in the presence of primary, secondary, and benzylic alcohols, O-methyl oximes, tosylhydrazones, and acid sensitive groups/moieties.

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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 enantioselective double Michael reaction of N-Boc-3-nonsubstitued oxindoles with dienones catalyzed by chiral monoimide protected cyclohexane-1,2-diamines was developed. A wide range of optically active spirocyclic oxindoles were obtained up to 98% yield and up to 89% ee.

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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 one-pot synthesis of palladium nanoparticles supported on magnesium hydroxide fluoride has been performed with the fluorolytic sol-gel method. The prepared catalysts were characterized by using various physicochemical techniques. The sol-gel method led to high surface area (> 135 m2g-1), mesoporous catalysts (pore volume=0.19-0.23 cm3g-1, pore diameter= 3-5 nm) with uniformly dispersed palladium nanoparticles approximately 2 nm in diameter on the surface. The catalysts synthesized by using different concentrations of aqueous hydrofluoric acid exhibited changing surface and acidic properties. Very high dispersion of palladium on magnesium fluoride (47%) was obtained with 1 wt% palladium loading. The catalysts were used for hydrogenation of various olefins in the presence of other organic functionalities at room temperature and atmospheric hydrogen pressure. Various substituted olefins were hydrogenated with almost 100% conversion and selectivity. The catalysts were recycled efficiently over five cycles without appreciable loss in catalytic activity. There was no palladium leaching under the reaction conditions, which was confirmed by inductively coupled plasma atomic emission spectroscopy analysis. Activation of olefin on the catalyst surface could not be observed by in situ FTIR studies, indicating facile activation of hydrogen on the palladium supported on magnesium hydroxide fluoride.

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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 tributylphosphine-catalyzed bis-Michael addition reaction of various kinds of alpha,beta-unsaturated carbonyl compounds with active methylenes is described. This is a convenient and rapid method for generating quaternary carbons centers and useful procedure for the synthesis of branched core and highly substituted trans cyclohexanones. All the reactions were completed in 60 min and afford the corresponding products in excellent yields.

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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 new nucleophilic isopropyl transfer reagent, triisopropylsulfoxonium tetrafluoroborate, has been prepared and evaluated. Thus, using this reagent and NaH in DMF, a range of electron deficient alkenes, including several chalcone analogues, alpha,beta-unsaturated ketones, dienones and quinones, plus alpha,beta-unsaturated esters, nitrile, sulfone and nitro examples, have been converted into the corresponding gem-dimethylcyclopropane compounds.

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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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Base-catalyzed C?C cross coupling of secondary alcohols and aryl-aldehydes was achieved, when an alcoholic solution of an aryl-aldehyde was stirred under reflux for 45 h in the presence of a catalytic (20 mol%) amount of K2CO3. The consistent formation of alpha,alpha?-bis-(benzylidene) alkanones was obtained in moderate to good yields using various secondary alcohols and substituted aryl-aldehydes. Herein, alpha,alpha?-bis-(benzylidene)alkanones, which are the classical products of Claisen-Schmidt (cross aldol) condensation, have been synthesized via an alternative strategy using secondary alcohols. Bis-(benzylidene) alkanones are an integral part of various drug regimes and the production of bis-(benzylidene) alkanones without using any precious metal is a major outcome of the present reaction.

A reaction mechanism is the microscopic path by which reactants are transformed into products. Each step is an elementary reaction. In my other articles, you can also check out more blogs about 538-58-9

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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Aromatic aldehydes undergo crossed-aldol condensation with ketones in the presence of catalytic amount of sulfamic acid (SA) to afford the corresponding alpha, beta-unsaturated aldol products under solvent-free conditions in good to high yields at 45-80 C.

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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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Two different enantioselective organocatalytic cascade reactions to form new sulfur-containing spirocyclic scaffolds are described. In the first approach, benzothiophen-2-one and enals react in the presence of a secondary amine catalyst through a Michael/Michael/Aldol sequence to afford the final spiro-cyclohexene carbaldehydes in good yields (up to 68 %) and with excellent selectivities [20:1 diastereomeric ratio (dr), up to 99 % ee]. In the second approach, the double Michael addition of benzothiophen-2-one to aromatic dienones with primary amine catalysis produces the corresponding spiro-cyclohexanones in good yields (up to 76 %) and with moderate-to-high selectivities (up to 12:1 dr, up to 90 % ee). Moreover, the use of N-phenylrhodanine as the bis-nucleophile for these reactions also allowed the formation of the corresponding spirocyclic adducts. Benzothiophenone and N-phenylrhodanine were successfully used as bis-nucleophiles in two enantioselective organocatalytic cascades. Their reactions with enals and dienones allowed the formation of new sulfur-containing spirocyclic scaffolds in good yields and with high selectivities. Copyright

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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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Fluorination followed by the Michael addition or Robinson annulation of 1,3-dicarbonyl compounds is introduced for the synthesis of acyclic and cyclic alpha-fluoro-beta-ketoesters and alpha-fluoro-1,3-diketones. The decarboxylation step can also be added to the reaction sequence. High efficiency is achieved by the microwave heating and atom economic one-pot synthesis.

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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