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    Tricyclic ortho ester formation from trichloroethylidene acetals of sugars via ketene acetals
    Tetrahedron Letters (1994)
    Yeşim Gül SalmanÖmür MakinabakanLevent Yüceer
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    Keywords:
    Tricyclic
    Arabinose
    Topics:
    Diet, Metabolism, and Disease
    Tricyclic ortho ester formation from trichloroethylidene acetals of sugars via ketene acetals
    Tetrahedron Letters (1994)
    Yeşim Gül SalmanÖmür MakinabakanLevent Yüceer
    Tricyclic
    Arabinose
    Citations (20)
    Etude de la reaction chlorocarbene-acetals de cetenes
    Tetrahedron (1985)
    G. ROUSSEAUN. Slougui
    Carbenoid
    Citations (5)
    ChemInform Abstract: Chemistry of Amino Ketene Dithioacetals: Preparation of Protected α‐Amino Aldehydes and Ketones and Formation of Nitrogen Heterocycles.
    ChemInform (1987)
    P. C. B. PageMonique B. van NielDonald Westwood
    Abstract The enamine (I) is transformed into the α‐methyl ketone (III) by lithiation, methylation, and subsequent hydrolysis.
    Citations (0)
    Two-Carbon Homologation of Aldehydes via Silyl Ketene Acetals: A New Stereoselective Approach to (E)-Alkenoic Acids
    The Journal of Organic Chemistry (1998)
    Moncef BellassouedNathalie LensenM. BakasseSinda Mouelhi
    Aldehydes are converted into (E)-α,β-unsaturated carboxylic acids using C,O,O-tris(trimethylsilyl)ketene acetal 1. This organosilicon reagent is easily generated from trimethylsilyl acetate, LDA, and chlorotrimethylsilane. The effectiveness of the reaction has been explored for a large variety of aldehydes with Lewis acids and fluorides as catalysts.
    Organosilicon
    Trimethylsilyl
    Citations (24)
    Stereoselective Synthesis of Ketene Silyl Acetals
    Synlett (1994)
    Junzo OteraYukihiro FujitaShunich Fukuzumi
    Synthesis of ketene silyl acetals with high (E)- and (Z)-stereochemistry is achieved by increasing the size of alkoxy group or by employing an excess amount of esters over LDA.
    Citations (19)
    Stereoselective routes to substituted β-amino carbonyl compounds via heterodiene cycloadditions of an auxiliary-based C2-symmetric ketene acetal
    Tetrahedron Letters (2000)
    Colin RayTimothy W. WallaceRichard A. Ward
    Methylene
    Citations (20)
    Highly 1,2-trans Stereoselective Allylations of 1,2-O-Isopropylidene-Protected Glycofuranosides
    Angewandte Chemie International Edition (2000)
    Fernando García‐TelladoPedro de ArmasJosé Juan Marrero‐Tellado
    A remarkable bicyclic acetal template effect is responsible for the complete 1,2-trans stereoselectivity achieved in Lewis acid promoted allylations of 1,2-O-isopropylidene-protected furanosides [Eq. (1)]. This stereoselectivity occurs regardless of the other substituents on the tetrahydrofuran ring. The bicyclic acetal acts as a basic, stable anomeric protecting group, and activates the carbohydrate anomeric position and directs the stereochemical outcome of the substitution reaction at this center.
    Tetrahydrofuran
    Protecting group
    Citations (29)
    Two-Carbon Homologation of Aldehydes via Silyl Ketene Acetals. 2.1 Study of the Stereochemical Control in the Formation of (E)-Alkenoic Acids
    The Journal of Organic Chemistry (2001)
    Moncef BellassouedSinda MouelhiNathalie Lensen
    The condensation of C,O,O-tris(trimethylsilyl)ketene acetal 1 with aldehydes 2 in the presence of catalytic amounts of mercuric iodide at room temperature affords syn and anti beta-trimethylsiloxy alpha-trimethylsilyl alkanoic acid silyl esters 3 in good yields. These new compounds gave, under acidic or basic conditions, E and (or) Z enoic acids 4. The paths for the formation of these alkenoic acids are discussed.
    Trimethylsilyl
    Methyl iodide
    Citations (11)
    Ketene Acetal and Spiroacetal Constituents of the Marine Fungus Aigialus parvus BCC 5311
    Journal of Natural Products (2004)
    Pornrapee VongvilaiMasahiko IsakaPrasat KittakoopPrasert SrikitikulchaiPalangpon Kongsaeree
    Aigialone (1) and aigialospirol (2), two structurally unique compounds, were isolated from the mangrove fungus Aigialus parvus BCC 5311. The structure of the new ketene acetal 1 was elucidated by spectral analysis, and its relative stereochemistry was determined by X-ray crystallography. The stereochemistry of aigialospirol (2), elucidated by NMR spectral analysis, suggested that this compound is possibly derived from hypothemycin (3), a metabolite previously isolated from this same fungus.
    Spectral Analysis
    Citations (33)
    Triethylsilylation of hydroxyl groups with a ketene triethylsilyl acetal. 2-Methyl-1-triethylsilyloxy-1-methoxypropene.
    Chemical and Pharmaceutical Bulletin (1983)
    Eiichi YoshiiKei Takeda
    A convenient O-triethylsilylation with dimethylketene triethylsilyl methyl acetal (1), which is prepared in excellent yield by catalytic hydrosilylation of methyl metacrylate is reported. Primary alcohols react readily at room temperature. Hindered alcohols are rapidly silylated in the presence of a trace amount of trifluoromethanesulfonic acid. For phenols heating with or without solvent is required.
    Hydrosilylation
    Citations (9)