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An efficient construction of bicyclic systems containing a seven-membered ring by tandem ring-closing metathesis reactions of dienynes

Various (5-7) and (6-7) bicyclic dienes bearing quaternary methyl group and ester functionality have been synthesized from acyclic dienynes by tandem ring-closing metathesis (RCM) reaction. Epoxidation of these conjugated dienes led to bicyclic vinyl oxiranes which undergo acid-catalyzed addition of alcohols to afford highly oxygenated compounds.

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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity

The molecular design, chemical synthesis, and biological evaluation of two distinct series of platensimycin analogues with varying degrees of complexity are described. The first series of compounds probes the biological importance of the benzoic acid subunit of the molecule, while the second series explores the tetracyclic cage domain. The biological data obtained reveal that, while the substituted benzoic acid domain of platensimycin is a highly conserved structural motif within the active compounds with strict functional group requirements, the cage domain of the molecule can tolerate considerable structural modifications without losing biological action. These findings refine our present understanding of theplatensimycin pharmacophore and establish certain structure-activity re lationships from which the next generation of designed analogues of thisnew antibiotic may emerge.

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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Synthesis of substituted cycloalkene-1,1-dicarboxylates via olefin metathesis in water

A range of substituted cycloalkene-1,1-dicarboxylates was synthesized through olefin metathesis starting from readily available acylic malonate precursors in an efficient fashion. As a metathesis catalyst, a Grubbs II-type catalyst was used in these experiments, which were run in water and gave the cyclic malonate products with high conversions of 94-100%. The catalytic amount was in the range of 0.5-5 mol% dependent on the structure of the starting material. The generality of this metathesis reaction in water was demonstrated as well as its suitability for the preparation of five and six-membered and alkyl as well as aryl-substituted prochiral cycloalkene-1,1-dicarboxylates.

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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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METHOD OF PRODUCING OLEFINS VIA METATHESIS

Disclosed is a method of producing an organic compound. The method uses a metathesis catalyst in a coupling reaction of an olefin. The method comprises the steps of introducing the olefin into a container; either placing the container under vacuum or bubbling a gas through the olefin; adding an additive with the olefin; mixing the olefin and the additive, the mixing creating a mixture; adding an amount of the metathesis catalyst to the mixture, the amount being less than about 100 ppm by weight of the mixture; and optionally heating the mixture to a temperature, the temperature being greater than room temperature.

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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Ruthenium-catalyzed ring-closing metathesis accelerated by long-range steric effect

Ruthenium-based metathesis catalysts with a N-heterocyclic carbene ligand bearing 2,3,4,5-tetraphenylphenyl moieties (1-TPPh and 1-TPPh*) are developed. The highly active catalyst system has been realized in THF by the combination of 1-TPPh* and CuCl as a phosphine scavenger. The Royal Society of Chemistry 2011.

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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Chiral approach to total synthesis of phytotoxic and related nonenolides: (Z)-isomer of (6S,7R,9R)-6,7-dihydroxy-9-propylnon-4-eno-9-lactone, herbarumin-III and their C-9 epimers

A new and efficient strategy has been developed for the stereoselective total synthesis of nonenolides: (Z)-isomer of (6S,7R,9R)-6,7-dihydroxy-9-propylnon-4-eno-9-lactone, herbarumin-III and their C-9 epimers starting from D (?) ribose. The synthesis includes the coupling of the alcohol and acid fragments of the molecules, employing Yamaguchi esterification protocol followed by intramolecular ring closure metathesis. The method has efficiently constructed the 10-membered lactone skeleton of the compounds with proper stereogenic centers containing appropriate functionalities.

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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Total synthesis of (-)-archazolid B

A highly convergent synthesis of archazolid B, a potent and highly selective V-ATPase inhibitor, is described. A relay ring-closing metathesis reaction was used to form the 24-membered macrocyclic lactone, whereas the sensitive cis-triene moiety of the archazolids was assembled with a modified Stille coupling. Copyright

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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Synthesis of bicyclic nucleosides by ring-closing metathesis

The ring-closing metathesis method is applied in the construction of conformationally restricted bicyclic nucleosides. From diacetone-D-glucose, the unsaturated bicyclic carbohydrate derivative 11 is efficiently obtained through two vinyl group Grignard additions, subsequent metathesis of the double bonds, and resolution of the stereochemistry by an oxidation/reduction reaction sequence. Two separate routes differing in the 3-O-protecting group are compared. Thus, an additional protecting step improves the yields significantly. Standard conversions of 11 give the bicyclic nucleoside 22 containing an olefinic moiety with a high potential for further functionalisation. As examples, two simple bicyclic ribo-nucleoside analogues 4 and 5, which are restricted to the unusual South-type conformations, are synthesised.

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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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PREPARATION OF SURFACTANTS VIA CROSS-METATHESIS

The present invention relates to compositions comprising 2-phenyl linear alkene benzenes or 2-phenyl linear alkene benzene sulfonates or 2-phenyl linear alkylbenzenes or 2-phenyl linear alkylbenzene sulfonates; where the benzene ring is optionally substituted with one or more groups designated R *, where R * is defined herein and to methods for making the same. This invention also relates to compositions, methods of making, use of, and articles of manufacuture comprising 2-ethoxylated hydroxymethylphenyl linear alkyl benzenes or 2-propoxylated hydroxymethylphenyl linear alkyl benzenes.

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Reference£º
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Kinetics and Mechanism of Isocyanide-Promoted Carbene Insertion into the Aryl Substituent of an N-Heterocyclic Carbene Ligand in Ruthenium-Based Metathesis Catalysts

In situ IR spectroscopy was used to study the kinetics of addition of L = alkyl and aryl isocyanides to the Grubbs second-generation carbene complex Ru(H2IMes)(CHPh)(PCy3)Cl2 (H2IMes = 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene), which triggers carbene insertion into an aromatic ring of the N-heterocyclic carbene supporting ligand, forming Ru{1-mesityl-3-(7?-Ph-2?,4?,6?-trimethylcycloheptatrienyl)-4,5-dihydroimidazol-2-ylidene}L2(PCy3)Cl2. The rate law was determined to be first order in isocyanide concentration and first order in carbene complex concentration. For various isocyanides CNR the rate increases as R = tert-butyl ? cyclohexyl < n-octyl < CH2Ph ? CH2CO2Me ? CH2SO2C6H4-4-Me < C6H4-4-OMe < C6H4-4-Cl. The proposed mechanism involves reversible addition of isocyanide followed by rate-determining, irreversible carbene insertion and subsequent, rapid addition of the second isocyanide. The carbene insertion is accelerated by the electrophilicity of the carbene, which is enhanced due to ligand binding by isocyanides with lower sigma-donor/pi-acceptor ratios. Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Recommanded Product: 246047-72-3. In my other articles, you can also check out more blogs about 246047-72-3

Reference£º
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI