92157-35-2

Upstream product

• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 123-11-5 4-methoxy-benzaldehyde 
• 151721-69-6 methyl 3-(4-methoxyphenyl)-2,2-dimethyl-3-trimethylsilyloxypropionate 

Relevant academic research and scientific papers

Cage Like Al-KIT-5 Mesoporous Materials for C-C Bond Formation Reactions under Solvent Free Conditions

The C-C bond forming reactions are of fundamental importance in chemistry. As a result there is ever growing interest for chemists to develop new methods for C-C bond formation. We report here three dimensional nano-cage mesoporous aluminosilicate materia

Mukaiyama aldol reactions catalyzed by a trimeric organo aluminum(III) alkoxide

Mukaiyama aldol reactions of enol ethers with a variety of aldehydes and ketones are efficiently catalyzed at 0-25 °C by the sterically bulky trimeric organo aluminum(III) alkoxide 1 synthesized via the reaction of 3 equiv of AlMe3 with tripodal tris(2-hydroxy-3-tert-butyl-5-methylphenyl) methane and the elimination of 3 equiv of methane. Comparisons of its catalytic properties with the less sterically hindered analogue 2, the more sterically hindered analogue 3, a monomeric aluminum near-analogue 4, and a dimeric alumatrane 5 revealed that 1 possesses superior activity.

Mukaiyama aldol reaction of trimethylsilyl enolate with aldehyde catalyzed by CuI

Cuprous iodide has been found to be a very effective catalyst for Mukaiyama aldol reaction of trimethylsilyl ketene acetal with aldehydes. The new catalytic system promotes efficiently the Mukaiyama aldol reaction in DMF to produce corresponding β-hydroxy carbonyl compounds in high yield.

Strong Lewis acids of air-stable metallocene bis(perfluorooctanesulfonate)s as high-efficiency catalysts for carbonyl-group transformation reactions

Strong Lewis acids of air-stable metallocene bis(perfluorooctanesulfonate)s [M(Cp)2][OSO2C8F17] 2·nH2O·THF (M=Zr (2 a·3 H 2O·THF), M=Ti (2 b·2 H2O·THF)) were synthesized by the reaction of [M(Cp)2]Cl2 (M=Zr (1 a), M=Ti (1 b)) with nBuLi and C8F17SO3H (2 equiv) or with C8F17SO3Ag (2 equiv). The hydrate numbers (n) of these complexes were variable, changing from 0 to 4 depending on conditions. In contrast to well-known metallocene triflates, these complexes suffered no change in open air for a year. thermogravimetry-differential scanning calorimetry (TG-DSC) analysis showed that 2 a and 2 b were thermally stable at 300 and 180 °C, respectively. These complexes exhibited unusually high solubility in polar organic solvents. Conductivity measurement showed that the complexes (2 a and 2 b) were ionic dissociation in CH3CN solution. X-ray analysis result confirmed 2 a·3 H2O·THF was a cationic organometallic Lewis acid. UV/Vis spectra showed a significant red shift due to the strong complex formation between 10-methylacridone and 2 a. Fluorescence spectra showed that the Lewis acidity of 2 a fell between those of Sc3+ (λem=474 nm) and Fe3+ (λem=478 nm). ESR spectra showed the Lewis acidity of 2 a (0.91 eV) was at the same level as that of Sc3+ (1.00 eV) and Y 3+ (0.85 eV), while the Lewis acidity of 2 b (1.06 eV) was larger than that of Sc3+ (1.00 eV) and Y3+ (0.85 eV). They showed high catalytic ability in carbonyl-compound transformation reactions, such as the Mannich reaction, the Mukaiyama aldol reaction, allylation of aldehydes, the Friedel-Crafts acylation of alkyl aromatic ethers, and cyclotrimerization of ketones. Moreover, the complexes possessed good reusability. On account of their excellent catalytic efficiency, stability, and reusability, the complexes will find broad catalytic applications in organic synthesis. Copyright

Catalysis of Mukaiyama aldol reactions by a tricyclic aluminum alkoxide Lewis acid

(Chemical Equation Presented) The Mukayiama aldol reaction of aldehydes is efficiently accomplished with a low concentration of the dimeric alumatrane catalyst 2 at mild or subambient temperatures. Our protocol tolerates a wide variety of electron-rich, neutral, and deficient aryl, alkyl, and heterocyclic aldehydes. A wide variety of enol silyl ethers are also tolerated. An intermediate that was isolated provides mechanistic information regarding the role of dimeric 2 in the Mukaiyama aldol reaction. Experimental evidence is presented for the stronger Lewis acidity of 5 compared with F3B.

P(PhCH2NCH2CH2)3N catalysis of Mukaiyama aldol reactions of aliphatic, aromatic, and heterocyclic aldehydes and trifluoromethyl phenyl ketone

(Chemical Equation Presented) Herein we find that proazaphosphatrane 1c is a very efficient catalyst for Mukaiyama aldol reactions of aldehydes with trimethylsilyl enolates in THF solvent. Only the activated ketone 2,2,2-trifluoroacetophenone underwent clean aldol product formation with a variety of trimethylsilyl enolates under similar conditions as the aldehydes. The reactions were carried out at room temperature using (1-methoxy-2-methyl-1- propenyloxy)trimethylsilane, whereas the temperature was -15 °C in the case of 1-phenyl-1-(trimethylsilyloxy)ethylene. The reaction conditions are mild and operationally simple, and a variety of aryl functional groups, such as nitro, amino, ester, chloro, trifluoromethyl, bromo, iodo, cyano, and fluoro groups, are tolerated. Product yields are generally better than or comparable to those in the literature. 1-Phenyl-1-(trimethylsilyloxy)ethylene, 1-(trimethylsilyloxy) cyclohexene, and 2-(trimethylsilyloxy)furan underwent clean conversion to β-hydroxy carbonyl compounds under our reaction conditions. In the case of bulky (2,2-dimethyl-1-methylenepropoxy)trimethylsilane, only α,β-unsaturated esters were isolated. Heterocyclic aldehydes, such as pyridine-2-carboxaldehyde, benzofuran-2-carboxaldehyde, benzothiophene-2- carboxaldehyde, and 1-methyl-2-imidazolecarboxaldehyde, gave good yields of Mukaiyama products. An optimized synthesis for the catalyst 1c is also reported herein. 2009 American Chemical Society.

Synthesis and structure of an extremely air-stable binuclear hafnocene perfluorooctanesulfonate complex and its use in lewis acid-catalyzed reactions

An extremely air-stable μ2-hydroxy-bridged binuclear hafonocene perfluorooctanesulfoante complex was successfully synthesized. This complex showed high catalytic efficiency in the esterification of alcohols, phenol, thiol, and amines, in the Friedel-Crafts acylation of alylaryl ethers, in the Mukaiyama aldol reaction, and in the allylation of aldehydes and could be reused.

N-heterocyclic carbene-catalyzed Mukaiyama aldol reactions

(Chemical Equation Presented) N-Heterocyclic carbenes were shown to be highly effective catalysts to promote Mukaiyama aldol reactions. In the presence of only 0.5 mol % of N-heterocyclic carbene (5), various aldehydes and 2,2,2-trifluoroacetophenone unde

Practical aldol reaction of trimethylsilyl enolate with aldehyde catalyzed by N-methylimidazole as a Lewis base catalyst

Aldol reaction of trimethylsilyl enolate with aldehyde proceeded in the presence of a catalytic amount of a Lewis base, N-methylimidazole, and lithium chloride in DMF at room temperature. Not only aryl aldehyde but also alkyl aldehyde provided the aldol p

Aldol reaction of trimethylsilyl enolate with aldehyde catalyzed by pyridine N-oxide as a Lewis base catalyst

Aldol reaction of trimethylsilyl enolate with aldehydes proceeded in the presence of a catalytic amount of a Lewis base, pyridine N-oxide, and lithium chloride in DMF at room temperature. Not only aryl aldehydes but also alkyl aldehydes provided the aldol