Sequential reactions of Michael addition and Peterson condensation of 1-silylvinyl ketones with Grignard reagents: Study of stereoselectivity.
スポンサーリンク
概要
- 論文の詳細を見る
1-Silylvinyl ketones undergo smooth Michael addition with Grignard reagents generating magnesium enolates which are then trapped with benzaldehyde to give <I>E</I>- and <I>Z</I>-isomers of enones after Peterson condensation. (<I>E</I>)-Olefins become major products under a thermodynamic control when the condensation with benzaldehyde is carried out at room temperature in diethyl ether, while <I>Z</I>-isomers are more favored as kinetically controlled products at −78 °C in THF. Reaction mechanism is briefly discussed.
- 公益社団法人 日本化学会の論文
著者
-
Kanemasa Shuji
Institute Of Advanced Material Study Kyushu University
-
Kobayashi Hiroshi
Institute Of Advanced Biomedical Engineering And Science Tokyo Women's Medical University
-
Tanaka Junji
Institute Of Advanced Material Study Kyushu University
-
Tsuge Otohiko
Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences
-
Tanaka Junji
Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
関連論文
- Fibroblast sheets co-cultured with endothelial progenitor cells improve cardiac function of infarcted hearts
- Evaluation of Lewis Acidity of "Naked"Lithium Ion through Diels-Alder Reaction Catalyzed by Lithium TFPB in Nonpolar Organic Solvents
- Metal Bis((perfluoroalkyl)sulfonyl)amides as Novel Lewis Acid Catalysts in Diels-Alder Reaction
- Fibroblast Cell Sheets Co-cultured with Endothelial Progenitor Cells Improve Cardiac Function of Infarcted Heart(Tissue Engineering (H), The 69th Annual Scientific Meeting of the Japanese Circulation Society)
- Chiral Lewis Acid-Catalyzed Asymmetric Hetero Diels-Alder Reaction of (E)-2-Oxo-1-phenylsulfonyl-3-alkenes with Vinyl Ethers
- (E)-2-Oxo-1-sulfonyl-3-alkenes as Reactive Hetero 1,3-Dienes. Absolutely endo-Selective Hetero Diels-Alder Reactions with Vinyl Ethers in the Presence of a Lewis Acid Catalyst
- Magnesium Bromide-Promoted E/Z-Isomerization of Carbonyl-Conjugated Nitrones and Highly Stereo-and Regioselective Cycloadditions to Allylic Alcohol Dipolarophiles
- Collisional process on Comet 9/P Tempel 1 : mass loss of its dust and ice by impacts of asteroidal objects and its collisional history
- Chiral Lewis Acid-Catalyzed Asymmetric Diels-Alder Reactions of (E)-1-Phenylsulfonyl-3-alken-2-ones with Cyclopentadiene
- Bisoxazoline and Bioxazoline Chiral Ligands Bearing 4-Diphenylmethyl Shielding Substituents. Diels : Alder Reaction of Cyclopentadiene with 3-Acryloyl-2-oxazolidinone Catalyzed by the Aqua Nickel(II) Complex
- Ice sublimation of dust particles and their detection in the outer solar system
- Unusual Diastereofacial Selectivity in the Michael Addition Reactions of Lithiated 2-Aminoacetates and -acetamides to α,β-Unsaturated Carbonyl Compounds
- Planets in orbit around β Pictoris formed the orbital architecture of planetesimal belts?
- Catalyzed Enantioselective Conjugate Addition Reactions of Strongly Coordinating Nucleophiles
- Algicidal Activity of Glycerolipids from Brown Alga Ishige sinicola toward Red Tide Microalgae
- Simple generation of ester-stabilized azomethine ylides from 2-amino esters and carbonyl compounds. Stereochemistry of their cycloadditions.
- One-pot ortho hydroxylations of 2-(1-hydroxyalkyl)-naphthalenes and (1-hydroxyalkyl)benzenes.
- New synthesis of 2-oxo-3-alkenylphosphonates and hetero Diels-Alder reactions with vinyl ethers leading to 5-substituted 2-phosphinyl-2-cyclohexen-1-ones.
- Hydroalumination and related reactions of phenyl 1-(trimethylsilyl)propadienyl sulfide followed by quenching with carbonyl compounds.
- Michael addition of methyl 2-(trimethylsilyl)propenoate with organomagnesiums or organolithiums leading to 1:1 and/or 2:1 adducts and subsequent Peterson olefination by condensation with carbonyl compounds.
- Stereoselective synthesis of [1]benzopyrano[4,3-b]pyrrol-4(3H)-ones through cycloadditions of azomethine ylides with .ALPHA.,.BETA.-unsaturated esters.
- Michael addition and alkylation of 2-azaallyl anions derived from N-(1-cyanoalkyl)imines, and stereoselective cyclization of imine esters or ketones leading to 1-pyrrolines.
- A michael addition and alkylation sequence using methyl 2-(trimethylsilyl)propenoate. Stereoselective synthesis of .ALPHA.-silyl esters.
- Asymmetric Dipolar Cycloaddition of Nitrile Oxides to the .ALPHA.,.BETA.-Unsaturated Esters Bearing an Imidazolidine Chiral Controller at the .BETA.-Position.
- Synthesis of substituted pyridines by a cycloaddition route using nitrile oxides and homoallyl alcohols.
- Acid-catalyzed transformation of .ALPHA.-hydroxy-.GAMMA.-oxo acetals to .GAMMA.-oxo esters. A novel deconjugation of 4-oxo-2-alkenal acetals.
- Intramolecular Cycloaddition of the Azomethine Ylides Derived from α-Amino Acids or Esters and 5-Oxo-6-heptenals or 4-Oxo-5-hexenals
- Sequential reactions of Michael addition and Peterson condensation of 1-silylvinyl ketones with Grignard reagents: Study of stereoselectivity.
- Asymmetric cycloaddition of N-metalated azomethine ylides with the optically active .ALPHA.,.BETA.-unsaturated esters derived from .ALPHA.-amino acids.
- Asymmetric Michael Addition of the N-Alkylidene Derivative of an .ALPHA.-Amino Ester to Methyl(E)-3-((3R, 7aS)-2-Phenylperhydropyrrolo(1,2-c)imidazol-3-yl)propenoate.
- Diene-transmissive hetero Diels-Alder reactions of 3-oxo-1,4-pentadiene equivalents leading to functionalized 2-chromanones.
- Michael Addition of Acyclic Lithium 1,3-Dien-2-olates with .ALPHA.,.BETA.-Unsaturated Esters, Ketones, and Diesters.
- Triethylamine-mediated generation of a synthetic equivalent of parent azomethine imine by condensation of ethyl 3-benzylcarbazate with paraformaldehyde.
- Horner-Emmons olefination of 4-hydroxy-2-oxoalkylphosphonates and related compounds: Applications to the syntheses of (.+-.)-gingerol, (.+-.)-yashabushiketol, and (.+-.)-dihydroyashabushiketol.
- Simple generation of nonstabilized azomethine ylides through decarboxylative condensation of .ALPHA.-amino acids with carbonyl compounds via 5-oxazolidinone intermediates.
- Cycloaddition reactions of highly stablized isoquinolinium methylides to nonactivated olefins and electron-rich olefins.
- Synthesis of 2-(1-phosphorylalkyl)- and 2-(1-alkenyl)furans through nitrile oxide cycloaddition route.
- Generation of an N-sodioazomethine ylide and its cycloadditions with .ALPHA.,.BETA.-unsaturated esters.
- Synthesis of (diethoxyphosphoryl)acetonitrile oxide and its cycloaddition to olefins. Synthetic applications to 3,5-disubstituted 2-isoxazolines.
- Synthesis of 4-[(E)-1-alkenyl]-2-hydroxybutanolides and (Z)-4-alkylidene-2-butenolides through cycloadditions using a phosphorus-functionalized nitrile oxide.