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8.15 : Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.

The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an asymmetric hydrogenation process using chiral homogeneous catalysts. The chiral catalysts are designed such that the metal coordinates to a chiral ligand. The most frequently used chiral ligand is BINAP [(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl] — a chelating diphosphine. The metal coordinates to the two phosphorus atoms of BINAP, creating a chiral environment for itself. Such chiral catalysts have tremendous applications in pharmaceutical industries, such as the asymmetric synthesis of (S)-naproxen, an anti-inflammatory drug molecule, and the synthesis of L-dopa, a drug used to treat patients with Parkinson's disease.

Asymmetric hydrogenation is specific to the type of double bond undergoing reduction. The presence of a functional group directly adjacent to the target double bond is essential for the hydrogenation process as it aids with effective coordination of the metal.

Tags
AlkenesCatalytic HydrogenationReductionTransition metal CatalystMolecular HydrogenSyn StereochemistryHeterogeneous CatalystHomogeneous CatalystChiral CenterEnantiomeric ProductsEnantioselective ReactionAsymmetric HydrogenationChiral Homogeneous CatalystsChiral LigandBINAPDiphosphinePharmaceutical IndustriesS naproxenL dopa

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8.15 : Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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8.1 : Regioselectivity of Electrophilic Additions-Peroxide Effect

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8.2 : Free-Radical Chain Reaction and Polymerization of Alkenes

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8.3 : Halogenation of Alkenes

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8.4 : Formation of Halohydrin from Alkenes

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8.5 : Acid-Catalyzed Hydration of Alkenes

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8.6 : Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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8.7 : Oxymercuration-Reduction of Alkenes

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8.8 : Hydroboration-Oxidation of Alkenes

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8.9 : Regioselectivity and Stereochemistry of Hydroboration

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8.10 : Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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8.11 : Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

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8.12 : Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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8.13 : Oxidative Cleavage of Alkenes: Ozonolysis

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8.14 : Reduction of Alkenes: Catalytic Hydrogenation

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