Baeyer-Villiger oxidation with Me3SiOOSiMe3 under assistance of SnCl4 or BF3OEt2.

スポンサーリンク

概要

• 論文の詳細を見る

• Treatment of ketones with bis(trimethylsilyl) peroxide and Lewis acid such as SnCl<SUB>4</SUB> or BF<SUB>3</SUB>·OEt<SUB>2</SUB> in dichloromcthane at room temperature affords esters in fair to excellent yields. Jasmine lactone is synthesized from 2-[(<I>Z</I>)-2-pentenyl]cyclopentanone by means of Me<SUB>3</SUB>SiOOSiMe<SUB>3</SUB>–BF<SUB>3</SUB>·OEt<SUB>2</SUB> system without any protection of the carbon-carbon double bond. The oxidation of enol acetates of ketones to α-hydroxy (or α-acetoxy) ketones with Me<SUB>3</SUB>SiOOSiMe<SUB>3</SUB>–FeCl<SUB>3</SUB> system is also disclosed.

• 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

• Nozaki Hitosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Matsubara Seijiro

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

関連論文

• Fullerene and Sulfur Compounds
• Improved Synthesis and Crystal Structure of TiCl_3 (tmeda) (thf): A Highly Stereoselective Pinacol Coupling Reagent for Aromatic Aldehydes
• Preparation of Deuterium Labelled Organophosphonium Salts (Wittig Salts) under Hydrothermal Condition Catalyzed by Molecular Sieves
• Ruthenium-catalyzed Isomerization of Alkenol into Alkanone in Water under Irradiation of Microwaves
• Allylation of Carbonyl Compounds with Allylic Gallium Reagents
• Carbazole Synthesis by Platinum-catalyzed C-H Functionalizing Reaction Using Water as Reoxidizing Reagent
• Preparation of Organoytterbium Reagent from Ytterbium Trichloride and Organomagnesium
• Preparation of Ester-group Substituted Allylic Zinc by Palladium-catalyzed Umpolung of γ-Acyloxy-α,β-unsaturated Ester by Bis(iodozincio)methane
• Nickel-catalyzed [4+2] Cycloaddition of Alkynes to Carbonylsalicylamides via Elimination of Isocyanates
• 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
• Preparation and Reaction of Phenylsulfonyl-substituted Dizinciomethane
• 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
• Stereocontrolled Reduction of 2-Acyl-1,3-oxathiane Derivatives by Zn(BH_4)_2 and YCl_3-NaBH_4
• Sequential Introduction of Carbon Nucleophiles onto Silicon Atoms Using Methyl as a Leaving Group
• A Preparation of β-Oxoester Enolate Equivalents from SmI_2 and α-Bromoalkanoates
• Preparation of Dialkoxyborylbis(bromozincio)methane and Its Reaction with Electrophiles
• Wittig Type Methylenation of Ketones with Bis(iodozincio)methane and Ionic Liquid
• The Rate Enhancement Effect of Protodesilylation of Arylsilane Derivatives
• Iron(II) Chloride-mediated Addition of Dialkylmagnesium to Carbonyl Compounds
• Fabrication of Nano-structure by Diels-Alder Reaction
• Nickel-catalyzed Decarbonylative Cycloaddition of Phthalic Anhydrides with 1,3-Dienes
• Wittig Like Methylenation of Aldehydes in a Microflow System: Selective Methylenation by Differential of Plural Reactions
• Reaction of Tantalum-Alkyne Complexes with Hydrazones. Stereoselective Synthesis of (E)-Allylic Hydrazines.
• Methylenation of Esters with Bis(iodozincio)methane-TiCl_2-TMEDA System
• 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
• Nickel-catalyzed Cycloaddition of Aromatic (O-Benzyl)ketoximes with Alkynes to Produce Isoquinoline and Isoquinoline N-Oxide Derivatives
• Nickel-catalyzed Heteroannulation of o-Haloanilines with Alkynes
• 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
• Nickel-catalyzed Decarboxylative Polymerization of 6-Alkynylisatoic Anhydride
• Rapid Preparation of Cycloheptane Ring from 1,2-Diketone and Bis(iodozincio)methane via Oxy-Cope Rearrangement Using Microflow System
• 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.
• Condensation Reactions of Sulfonylcarbanion
• Synthesis and Reactions of Sulfonium Diacylmethylide Having Active Hydrogen
• Nickel-catalyzed Cycloaddition of α,β-Unsaturated Oximes with Alkynes : Synthesis of Highly Substituted Pyridine Derivatives
• 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
• Thermolysis and Photolysis of Benzopinacol Dicarboxylates
• The Reaction of O,O′-Diethyl α-Lithiomethylphosphonate with Organic Dihalides
• The Oxidation of Alkylbenzenes and Acylcarbinols by Means of Benzopinacol Diesters
• Cyclopentenone synthesis from 1,1-dichloroallyllithium-ketone adducts as well as from dichlorocarbene-allyl alcohol adducts.
• The Dehalogenation of Organic Halides by Means of Iron(II) Chloride in Dimethyl Sulfoxide
• Rearrangement of vic-diol monoacetates promoted by organoaluminium compounds.
• 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.
• Nickel-catalyzed Decarbonylative Polymerization of 5-Alkynylphthalimides : A New Methodology for the Preparation of Polyheterocycles
• The Syntheses and Reactions of Sulfenyl-substituted Sulfonium Ylides
• The Acid-Catalyzed Ring-Opening of Cyclooctenimine Derivatives
• Cr(III) or Ce(IV) impregnated perfluorinated resin-sulfonic acid catalyst for the oxidation of alcohols.
• A New Synthesis of Thiophenes
• Photoinduced Transannular Reaction of 4,5-Octamethylene-1,3-dioxolen-2-one
• The Reaction of Acyl-substituted Sulfonium and Pyridinium Ylides with Diphenylthiirene Dioxide
• Palladium-catalyzed ketone synthesis from acyl chloride and organoaluminum reagents.
• Preparation of 2-alkenylsilanes and 2-alkenylstannanes by the reaction of 2-alkenyl-1,1-cyclopropanedicarboxylate esters with PhMe2SiAlEt2 and (Ph3Sn)2Zn. Generation of 2-alkenyl-3-cyclopentene-1,1-decarboxylates via alkenyl-substituted .PI.-allylpalladiu
• Photochemistry of Non-enolizable β-Diketones Containing Cyclopropane Ring in Conjugation
• Copper-catalyzed 1,4-Addition Reaction of Grignard Reagent to Enones Using Microflow System

もっと見る 閉じる

スポンサーリンク