Reformatsky type reaction with new aluminium reagents containing Al-Sn or Al-Pb linkage.
スポンサーリンク
概要
- 論文の詳細を見る
Treatment of α-bromo carbonyl compounds with the reagent prepared from <I>n</I>-Bu<SUB>3</SUB>SnLi and Et<SUB>2</SUB>AlCl or from SnCl<SUB>2</SUB> and Et<SUB>2</SUB>AlCl affords enolates which react with ketone or aldehyde to give β-hydroxy carbonyl compounds in good to excellent yields. The reactions proceed similarly with the reagents which are generated from R<SUB>3</SUB>PbLi (R=Ph, <I>n</I>-Bu) and Et<SUB>2</SUB>AlCl. Catalysis by the added Pd(PPh<SUB>3</SUB>)<SUB>4</SUB> complex promotes the reduction effectively and improves the yields of the desired adducts. The regio- and stereoselectivities are disclosed.
- 公益社団法人 日本化学会の論文
著者
-
Oshima Koichiro
Department Of Industrial Chemistry Faculty Of Engineering Kyoto University
-
Nozaki Hitosi
Department of Industrial Chemistry, Faculty of Engineering Kyoto University
-
Morizawa Yoshitomi
Department of Industrial Chemistry, Faculty of Engineering Kyoto University
-
Matsubara Seijiro
Department of Industrial Chemistry, Faculty of Engineering Kyoto University
-
Tsuboniwa Noriyuki
Department of Industrial Chemistry, Faculty of Engineering Kyoto University
-
Oshima Koichiro
Department of Chemistry, Massachusetts Institute of Technology
関連論文
- 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
- 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
- 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
- Bis(cyclopentadienyldicarbonyliron) as a Convenient Carbon Monoxide Source in Palladium-catalyzed Carbonylative Coupling of Aryl Iodides with Amines, Alcohols, and Thiols
- 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.
- Alkylation of bromocyclopropanes and bromoarenes by means of dibutylcopperlithium and alkyl halides.
- A facile ring enlargement reaction via .BETA.-oxido carbenoid.
- The Reaction of Ethyl Azidoformate with Electron Deficient Olefins and the Thermal Ring Opening of the Resulting Aziridines.
- The Photolysis and Thermolysis of Ethyl Azidoformate in the Presence of Ketones
- A practical synthesis of polyhalomethyllithium-carbonyl adducts.
- Abnormal nazarov reaction. A new synthetic approach to 2,3-disubstituted 2-cyclopentenones.
- Tungsten hexachloride-catalyzed decomposition of diazo compounds. A novel oxazole synthesis.
- 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.
- Condensation Reactions of Sulfonylcarbanion
- Synthesis and Reactions of Sulfonium Diacylmethylide Having Active Hydrogen
- 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.
- The Nucleophilic Cyclopropylation of the Condensed Aromatic Ring with Sulf onylcarbanion
- Stereochemical studies on the nucleophilic substitution in the reaction of allylic phosphates with organoaluminum reagents.
- Synthesis of [9]Heterophanes from 2-Cyclododecenone
- Carbocyclic ring formation by the intramolecular reaction between enol silyl ether and allylic acetate moieties.
- Synthesis of homoallylic alcohols from allylic phosphates and aldehydes with organoaluminum reagent containing Al-Sn linkage.
- The 1-Methylene Derivatives of [7](2,6)Pyridinophane. Preparative and Conformational Studies
- The Absolute Configurations of 2-Phenylaziridine and Its Derivatives