57956-40-8

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 547-63-7 Methyl isobutyrate 
• 186581-53-3 diazomethane 
• 1209-06-9 (+/-)-2,2-Dimethyl-5-phenyl-1,3-pentanediol 
• 130822-13-8 3-hydroxy-2,2-dimethyl-5-phenylpentanoic acid 
• 501-52-0 3-Phenylpropionic acid 
• 56318-53-7 3-phenylpropanoic acid triethylsilyl ester 
• 1215225-73-2 dimethylphenylsilyl 3-phenylpropionate 
• 22767-95-9 1-methylethyl 3-phenylpropionoate 
• 2021-28-5 ethyl dihydrocinnamate 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 57956-46-4 methyl (4E)-2,2-dimethyl-5-phenyl-3-trimethylsilyloxypentanoate 

Downstream Products

• 54322-96-2 (+/-)-3-Hydroxy-2,2-dimethyl-5-phenylvaleraldehyde 
• 1209-06-9 (+/-)-2,2-Dimethyl-5-phenyl-1,3-pentanediol 

Relevant academic research and scientific papers

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

Development of an azanoradamantane-type nitroxyl radical catalyst for class-selective oxidation of alcohols

The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.

9-azanoradamantane N—oxyl compound and method for producing same, and organic oxidation catalyst and method for oxidizing alcohols using 9-azanoradamantane N—oxyl compound

An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.

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.

Direct use of esters in the Mukaiyama aldol reaction: A powerful and convenient alternative to aldehydes

An indium triiodide catalyst promoted the direct transformation from esters to β-hydroxycarbonyl compounds using hydrosilanes and silyl enolates by a one-stage process. Various esters were applicable, and the high chemoselectivity of this system brings compatibility to many functional groups: alkenyl, alkynyl, chloro, and hydroxy.

Fluorous surface-active distannoxane catalysts

Fluorous distannoxanes (XR2fSnOSnR2 fX)2·nH2O (Rf= C 6F13C2H4) (1: X= C8F 17SO3, n= 10; 4: X = Cl, n=

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.

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

Catalytic enantioselective Mukaiyama aldol reaction via a chiral indium(III)-pybox complex

A chiral indium(III) complex prepared from indium triflate and a pybox ligand has been developed to give good yields and enantioselectivities (up to 92% ee) in the addition of (1-methoxy-2-methyl-propenyloxy)-trimethylsilane to various aromatic and alipha