Isomerization of allylic alcohols catalyzed by vanadium or molybdenum complexes.

スポンサーリンク

概要

• 論文の詳細を見る

• Isomerization of primary allylic alcohols proceeds in dichloromethane at 25 °C in the presence of the catalyst prepared <I>in situ</I> from VO(acac)<SUB>2</SUB> or MoO<SUB>2</SUB>(acac)<SUB>2</SUB>, and Me<SUB>3</SUB>SiOOSiMe<SUB>3</SUB> to give tertiary isomers in good yields. The catalysts are also effective for the rearrangements of <I>sec.</I>→<I>tert.</I> allylic alcohols. The isomerization of an allenyl allylic alcohol, 6-methyl-1,2,5-heptatrien-4-ol, gives either (<I>E</I>)-2-methyl-3,5,6-heptatrien-2-ol or (<I>E</I>)-6-methyl-3,5-heptadien-2-one selectively depending on the reaction conditions.

• 公益社団法人 日本化学会の論文

著者

• Takai Kazuhiko

  Department Of Applied Chemistry Faculty Of Engineering Okayama University

• Oshima Koichiro

  Department Of Industrial Chemistry Faculty Of Engineering Kyoto University

• Nozaki Hitosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Matsubara Seijiro

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Okazoe Takashi

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

• Oshima Koichiro

  Department of Chemistry, Massachusetts Institute of Technology

関連論文

• Improved Synthesis and Crystal Structure of TiCl_3 (tmeda) (thf): A Highly Stereoselective Pinacol Coupling Reagent for Aromatic Aldehydes
• Copper-Catalyzed Arylation of Chlorosilanes with Grignard Reagents
• Palladium-catalyzed Mizoroki-Heck Reactions of 2-Methylene-1,3-dithiane 1-Oxide with Aryl Iodides
• Synthesis of β,γ-Unsaturated Ketones from Acid Chlorides through Carbon-Pentamethylcyclopentadienyl Bond Formation and Cleavage
• Synthesis of Prenylarenes and Related (Multisubstituted Allyl)arenes from Aryl Halides and Homoallyl Alcohols via Palladium-Catalyzed Retro-Allylation
• Selectivity in Organic Group Transfer in Reactions of Mixed Diorganomanganese(II) and Triorganomanganate(II) with 2-Cyclohexen-1-one or Cyclohexanecarbaldehyde
• Manganese-Catalyzed Silylmagnesiation of Acetylenes and 1,3-Dienes
• Manganese-catalyzed Phenylation of Acetylenic Compounds with a Phenyl Grignard Reagent
• Preparation of Deuterium Labelled Organophosphonium Salts (Wittig Salts) under Hydrothermal Condition Catalyzed by Molecular Sieves
• Vanadium-Catalyzed Cross-Coupling Reactions of Alkyl Halides with Aryl Grignard Reagents
• Trialkylmanganate Mediated Radical Addition of Triphenylgermane to Carbon-Carbon Multiple Bonds
• Ruthenium-catalyzed Isomerization of Alkenol into Alkanone in Water under Irradiation of Microwaves
• Radical Addition of α-Halo Ester to Homoallylic Gallium or Indium Species : Formation of Cyclopropane Derivatives
• Allylation of Carbonyl Compounds with Allylic Gallium Reagents
• Preparation of Organoytterbium Reagent from Ytterbium Trichloride and Organomagnesium
• Stereoselective Allylation of 3-Oxo Amides
• Ruthenium Catalyzed Deuterium Labelling of α-Carbon in Primary Alcohol and Primary/Secondary Amine in D_2O
• Palladium-Catalyzed H-D Exchange Reaction under Hydrothermal Condition
• S_N2 Type Hydrolysis of Secondary Alkyl Halides and Sulfonates in Hydrothermal Water
• Synthesis of Coordinatively Unsaturated Cobalt(II)-Alkyl Complexes Bearing Phosphorus-bridged [1.1]Ferrocenophanes
• Facile Preparation of Vicinal Allylsiloxy-and Vinylsiloxyhaloalkanes and Their Radical Cyclization Reaction
• Selective Cyclotrimerization of Acetylenes via Tantalum-Alkyne Complexes
• Alkylidenation of Ketones by gem-Dibromoalkane, SmI_2, and Sm in the Presence of Catalytic Amount of CrCl_3
• Ytterbium Catalyzed Oxidation of Alcohols to Aldehydes and Ketones by Means of Iodosylbenzene
• Tris(trimethylsilyl)silyl Radical Induced Bicyclization of 1,6-Dienes and 1,6-Enynes Providing 3,3-Bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes and 3-Silabicyclo[3.3.0]oct-1-enes
• 2-Lithio-2-trimethylsilyl-1-silacyclopentane as a Synthetic Equivalent of 1-Lithio-1,4-butanediol
• Radical Addition of Polyhaloalkanes to 2-Ethynyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Radical Addition of Alkyl Halides to 2-Methylene-1,3-dithiane Monoxide as a Ketene Equivalent
• Extended Pummerer Reaction of Arylketene Dithioacetal Monoxides with Aromatic Compounds by Means Trifluoromethanesulfonic Anhydride
• Triethylborane-Induced Radical Reaction of Alkynylgallium with α-Halo Carbonyl Compounds
• Triethylborane Induced Radical Reaction of Gallium Enolates with α-Halo Esters
• Tributylmanganate(II)-Mediated Cyclization of Enynes
• Bis(iodozincio)methane as a synthetic tool
• Wittig Type Methylenation of Ketones with Bis(iodozincio)methane and Ionic Liquid
• The Rate Enhancement Effect of Protodesilylation of Arylsilane Derivatives
• Fabrication of Nano-structure by Diels-Alder Reaction
• Synthesis of Pyrimidines via Base-induced Condensation of α-Chloro Oxime Derivatives
• Cobalt-catalyzed Cross-coupling Reactions of Aryl Bromides with Alkyl Grignard Reagents
• Regio- and Stereoselective Additions of Diphenyldithiophosphinic Acid to N-(1-Alkynyl)amides and 1-Alkynyl Sulfides
• Silylcupration and Copper-Catalyzed Carbomagnesiation of Ynamides : Application to Aza-Claisen Rearrangement
• Regio- and Stereoselective Hydrothiolation Reactions of Ynamides with Diphenyldithiophosphinic Acid : Straightforward Synthesis of Ketene N,S-Acetal Derivatives
• Transformations of N-Allyl-N-(phenylethynyl)arenesulfonamides into 2,2-Disubstituted 4-Pentenenitriles through Aza-Claisen Rearrangement that Follows Carbomagnesiation
• Cobalt-Catalyzed Allylzincations of Internal Alkynes
• Radical Cyclization of Allyl 2-Iodophenyl Ether,N,N-Diallyl-2-iodoaniline, and 2-Iodoethanal Acetal by Means of Trialkylmanganate(II)
• Rhodium-Catalyzed Reaction of 1-Alkynylphosphines with Water Yielding (E)-1-Alkenylphosphine Oxides
• Atom-transfer Radical Addition of α-Iodo Esters to 1-Alkynyl Sulfides
• Palladium-Catalyzed 1-Methylene-2-propenylation Reactions of Aryl Bromides with 3,4-Alkadien-1-ols via Carbon-Carbon Bond Cleavage for the Synthesis of 2-Aryl-1,3-butadiene Derivatives
• Efficient Aerobic Oxidation of Phosphines, Phosphites, and Sulfides by Using Trialkylborane
• Copper-Catalyzed Allylation of Alkyl Halides with Allylic Grignard Reagents
• Development of Radical Reactions with Zirconocene Complexes as Electron Transfer Reagents
• Nickel-catalyzed Carbometalation Reactions of [2-(1-Propynyl)phenyl]methanol with 1-Alkenylmagnesium Reagents
• Cobalt-catalyzed Cross-coupling Reaction of Chloropyridines with Grignard Reagents
• Radical Addition of 2-Iodoalkanamide or 2-Iodoalkanoic Acid to Alkenes with a Water-Soluble Radical Initiator Initiator in Aqueous Media: Facile Synthesis of γ-Lactones
• Reduction of Organic Halides with Tri-2-furylgermane: Stoichiometric and Catalytic Reduction
• Radical Cyclization of N-Allyl-2-halo Amide in Water
• Radical Cyclization Reaction Using a Combination of Phosphinic Acid and a Base in Aqueous Ethanol
• Three-step α-Acylation of (E)-Cinnamate Esters with Inversion of Stereochemistry through Formation and Cleavage of Carbon-Pentamethylcyclopentadienyl Bonds
• Metal-Mediated Retro-Allylation of Homoallyl Alcohols for Highly Selective Organic Synthesis
• Cobalt-Catalyzed Allylic Substitution Reaction of Allylic Ethers with Phenyl and Trimethylsilylmethyl Grignard Reagents
• Highly Selective Synthetic Reactions by the Combined Use of Organometallic Reagents and Radical Species
• Triethylborane-Induced Radical Reactions in Ionic Liquids
• Stereoselective Reduction of α,β-Epoxy Ketones into erythro-α,β-Epoxy Alcohols with Sodium Borohydride in the Presence of Calcium Chloride
• Manganese (II) Chloride-Catalyzed Alkylmagnesation of 2-Alkynylphenol
• Reaction of 1, 3-Dihalopropene with Trialkylmanganate
• Reaction of Tantalum-Alkyne Complexes with Hydrazones. Stereoselective Synthesis of (E)-Allylic Hydrazines.
• A Facile Synthesis of 1,1-Disilylethenes via Me_3MgLi-Induced Monomethylation of Dibromodisilylmethanes
• Reaction of Trialkyl(dibromomethyl)silanes or 1,2-Bis(dibromomethyl)benzene with Triorganomanganates. A Facile and Selective Synthesis of Alkenylsilanes and 1,2-Diaryl-1,2-dihydrobenzocyclobutenes
• Radical Reaction by a Combination of Phosphinic Acid and a Base in Aqueous Media
• Catalytic Performance of Tantalum-η^2-Alkyne Complexes [TaCl_3(R^1C≡CR^2)L_2] for Alkyne Cyclotrimerization
• Successive Carbon-Carbon Bond Formation by Sequential Generation of Radical and Anionic Species with Manganese and Catalytic Amounts of PbCl_2 and Me_3 SiCl
• Nucleophilic addition of organochromium reagents to carbonyl compounds
• Transformation of Aldehydes into (E)-1-Alkenylsilanes and (E)-1-Alkenylboronic Esters with a Catalytic Amount of a Chromium Salt
• Bis(cyclopentadienyldicarbonyliron) as a Convenient Carbon Monoxide Source in Palladium-catalyzed Carbonylative Coupling of Aryl Iodides with Amines, Alcohols, and Thiols
• Teritary Amine-Accelerated Allylgallation of Terminal Alkynes
• Activation of Manganese Metal with a Catalytic Amount of Lead and Me_3SiCl and Its Application to Organic Synthesis
• Triethylborane-induced hydrodehalogenation of organic halides by tin hydrides.
• Palladium Catalyzed Reaction of Silacyclobutanes with Acetylenes.
• Thiocarbonyl Ylides. Attempted Preparation and Related Reactions
• Preparative and Structural Studies of Kostanecki's Compound
• The Reduction of gem-Dibromocyclopropanes by Means of Chromium(II) Acetate or Potassium Pentacyanocobaltate
• Regiocontrolled formation of 4,5-dihydro-3(2H)-furanones from 2-butyne-1,4-diol derivatives. Synthesis of bullatenone and geiparvarin.
• Highly selective carbon-carbon bond forming reactions mediated by chromium(II) reagents.
• Cross-coupling reaction between enol phosphates and organoaluminium compounds in the presence of palladium(0) catalyst.
• The Reaction of Styryl Sulfoxides or Sulfones with Boranes
• Reaction of organoaluminium reagents with cyclopropylmethyl acetates and 2-vinylcyclopropane-1,1-dicarboxylate esters.
• 1-Bromo-2-ethoxycyclopropyllithium: A synthetic equivalent of 2-lithio- or 3-lithiopropenal. Application to the synthesis of juvenile hormone (JH-II), .BETA.-sinensal, and jasmonoids.
• A novel synthesis of .ALPHA.-methylene-.GAMMA.-butyrolactones.
• Isomerization of allylic alcohols catalyzed by vanadium or molybdenum complexes.
• Reformatsky type reaction with new aluminium reagents containing Al-Sn or Al-Pb linkage.
• New methods for the synthesis of 3(2H)-furanones and 2(5H)-furanones.
• Palladium catalyzed hydrostannylation and hydrogermylation of acetylenes.
• Hydrostannation and hydrogermylation of allenes.
• Measurements of double differential neutron emission cross sections for fusion reactor candidate elements.
• Intramolecular cyclization of nerol and the related attack of (Z)-allylic alcohol moiety on the terminal olefin linkage as induced by TiCl4-PhNHMe complex. Synthesis of nezukone.
• Stereochemical studies on the nucleophilic substitution in the reaction of allylic phosphates with organoaluminum reagents.
• Carbocyclic ring formation by the intramolecular reaction between enol silyl ether and allylic acetate moieties.
• Stereoselective epoxidation of allylic alcohols and dehydrogenative oxidation of secondary alcohols by means of t-butyl hydroperoxide and aluminium reagents.
• Baeyer-Villiger oxidation with Me3SiOOSiMe3 under assistance of SnCl4 or BF3OEt2.
• Chromium(VI) or ruthenium(II) complex catalysis in oxidation of alcohols to aldehydes and ketones by means of bis(trimethylsilyl) peroxide.
• Aliphatic Claisen rearrangement promoted by organoaluminium reagents.

もっと見る 閉じる

スポンサーリンク