10316-61-7Relevant academic research and scientific papers
Radical cyclization of epoxynitriles mediated by titanocene chloride
Fernández-Mateos,Burón, L. Mateos,Clemente, R. Rabanedo,Ramos Silvo, Ana I.,González, R. Rubio
, p. 1011 - 1014 (2004)
The reductive radical cyclization of β-, γ-, δ- and ε-epoxynitriles has been achieved using titanocene chloride. The reaction was regioselective and afforded cyclic β-hydroxyketones in good yield. The catalytic version of this radical cyclization is also
Aldol Synthesis with an Aqueous Solution of Formalin
Ozasa, Nobuko,Wadamoto, Manabu,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 2219 - 2221 (2003)
With an aqueous solution of formalin, aldol reaction of trimethylsilyl enol ether proceeds moderately using tetrabutylammonium fluoride (TBAF). Furthermore, catalytic asymmetric hydroxymethylation with trimethoxysilyl enol ether using water tolerant (R)-B
Scandium(Iii) fluoride as a novel catalyst for hydroxymethylation of dimethylsilyl enolates in aqueous media
Kokubo, Masaya,Kobayashi, Shu
, p. 1562 - 1564 (2008)
Hydroxymethylation of dimethylsilyl (DMS) enolates using aqueous formaldehyde solution is catalyzed by scandium(III) fluoride (ScF3) in aqueous media to give the corresponding β-hy-droxy ketones in good to excellent yields. Whilst the DMS enola
Lewis base catalysis by thiourea: N -bromosuccinimide-mediated oxidation of alcohols
Tripathi, Chandra Bhushan,Mukherjee, Santanu
experimental part, p. 1592 - 1598 (2012/03/11)
In recent times, (thio)urea derivatives have become synonymous with hydrogen bonding owing to their extensive applicability as small molecule organocatalysts. In this paper, another activation mode by thiourea derivatives, namely via Lewis base catalysis, is disclosed for the NBS-mediated oxidation of alcohols. The mild reaction conditions employed here is suitable for chemoselective oxidation of secondary alcohol in the presence of primary alcohol.
Lipase-catalyzed kinetic resolution of α-hydroxymethylcycloalkanones with a quaternary carbon center. Chemoenzymatic synthesis of chiral pseudoiridolactones
Guerrab, Zineb,Schweiger, Stefan,Daou, Boujemaa,Ahmar, Mohammed,Cazes, Bernard
experimental part, p. 1752 - 1757 (2010/10/21)
The resolution of α-alkyl-α-hydroxymethylcyclopentanones 1 and cyclohexanones 3 has been efficiently achieved by using lipase-catalyzed transesterification reactions with vinyl acetate as the acylating agent. The enantiomeric selectivities were dependent
Lewis acid catalysis in water with a hydrophilic substrate: Scandium-catalyzed hydroxymethylation with aqueous formaldehyde in water
Kokubo, Masaya,Ogawa, Chikako,Kobayashi, Shu
supporting information; experimental part, p. 6909 - 6911 (2009/04/06)
(Chemical Equation Presented) Synthesis in deep water: For the title reaction, which proceeds with high selectivities, acid-base interactions between the Sc catalyst and HCHO are important. The reaction was used in the synthesis of an odorant to demonstra
Lewis base-promoted aldol reaction of dimethylsilyl enolates in aqueous dimethylformamide: Use of calcium chloride as a Lewis base catalyst
Miura, Katsukiyo,Nakagawa, Takahiro,Hosomi, Akira
, p. 536 - 537 (2007/10/03)
In the presence of CaCl2, dimethylsilyl (DMS) enolates smoothly reacted with aldehydes under mild conditions to give aldol adducts in good to high yields. The catalytic activities of various metal and tetrabutylammonium salts have revealed that CaCl2 works as a Lewis base catalyst to activate DMS enolates. The CaCl2-promoted reaction proceeded even in the presence of water or in pure water. This catalytic system was applicable to the aldol reaction with aqueous aldehydes such as formalin. Copyright
Rare Earth Metal Complexes as Water-Tolerant Lewis Acid Catalysts in Organic Synthesis
Kobayashi,Hashiya,Ishitani,Moriwaki,Nagayama
, p. 193 - 202 (2007/10/03)
Rare earth metal triflates are stable in aqueous media and can act as Lewis acid catalysts in several carbon-carbon bond forming reactions. This article describes some of these reactions; aldol and Mannich-type reactions in aqueous solution, and Friedel-Crafts acylations and Fries rearrangement in organic solvents. The reactions proceeded smoothly in the presence of a catalytic amount of the triflate under mild conditions. Moreover, the catalysts could be recovered after the reactions were completed and could be reused.
Lanthanide Triflates as Water-Tolerant Lewis Acids. Activation of Commercial Formaldehyde Solution and Use in the Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous Media
Kobayashi, Shu,Hachiya, Iwao
, p. 3590 - 3596 (2007/10/02)
Lanthanide trifluoromethanesulfonates (triflates), especially ytterbium triflate (Yb(OTf)3), were found to be stable Lewis acids in water.In the presence of a catalytic amount of lanthanide triflate, formaldehyde in water solution (commercial formaldehyde
Stabilization of reactive aldehydes by complexation with methylaluminum bis(2,6-diphenylphenoxide) and their synthetic application
Maruoka, Keiji,Concepcion, Arnel B.,Murase, Noriaki,Oishi, Masataka,Hirayama, Naoki,Yamamoto, Hisashi
, p. 3943 - 3949 (2007/10/02)
Reactive aldehydes such as formaldehyde and α-chloro aldehydes can be successfully generated by treatment of readily available trioxane and α-chloro aldehyde trimers, respectively, with methylaluminum bis(2,6-diphenylphenoxide) (MAPH), and stabilized as their 1:1 coordination complexes with MAPH. The resulting CH2=O·MAPH complex reacts with a variety of olefins to furnish ene-reaction products with excellent regio- and stereoselectivities. In addition, this complex as well as α-chloro aldehyde-M APH complexes can be utilized as a stable source of gaseous formaldehyde and reactive α-chloro aldehydes, respectively, for the nucleophilic addition of various carbanions (organometallics, enolates, etc.). Formation of reactive aldehyde-MAPH complexes is firmly confirmed by 1H NMR spectroscopy. A space-filling model of aldehyde-M APH complexes implies that formaldehyde and α-chloro aldehydes coordinated with MAPH may be electronically stabilized by two parallel phenyl groups of aluminum ligands.
