37038-75-8

Upstream product

• 24506-17-0 3-hydroxy-3-phenylpropionamide 
• 925-90-6 ethylmagnesium bromide 
• 55134-83-3 5-phenyl-3-ethyl-Δ²-isoxazoline 
• 100-52-7 benzaldehyde 
• 78-93-3 butanone 
• 816-40-0 1-Bromo-2-butanone 
• 616-27-3 1-chlorobutan-2-one 
• 617-86-7 triethylsilane 
• 19159-61-6 1-phenyl-2-vinylcyclopropane 
• 75281-80-0 4,5-dimethyl-2-phenyl-(2α,4α,5β)-1,3-dioxolane 
• 10191-25-0 3-oxo-valeric acid 
• 83862-15-1 (S)-1-((1R,2R)-2-Hydroxy-1-methyl-propoxy)-1-phenyl-pentan-3-one 
• 83862-16-2 (2R,3R)-3-((S)-1-Phenyl-but-3-enyloxy)-butan-2-ol 
• 1024022-46-5 1-hydroxy-2-methyl-1,1-diphenyl-3-butanone 

Downstream Products

• 52167-82-5 5-Diethylsilyloxy-5-phenyl-3-pentanon 
• 3152-68-9 1-phenyl-pent-1-en-3-one 
• 100-52-7 benzaldehyde 
• 5764-85-2 Ethyl 3-hydroxy-3-phenylpropanoate 
• 121361-47-5 2-hydroxy-1-phenylethyl propionate 
• 10522-05-1 Propionic acid 2-hydroxy-2-phenyl-ethyl ester 
• 3152-68-9 (1E)-1-phenylpent-1-en-3-one 
• 82782-06-7 (Z)-1-phenylpent-1-en-3-one 

Relevant academic research and scientific papers

Bovine serum albumin-catalysed cross aldol condensation: Influence of ketone structure

Bovine serum albumin (BSA) catalyses the cross aldol condensation and proved to be catalytically active at mild temperature and in ethanol, a cheap and green solvent, contrasting with the strong or expensive reaction media usually employed for this reaction. We herein report the reaction of a set of ketones (butanone, 3-pentanone, cyclopentanone and cyclohexanone) with benzaldehyde and p-nitrobenzaldehyde which provided high conversions (77–95%) of the corresponding enones (isolated in a range of yields from 19% to 74%). Parameters assayed to achieve these conversion values were solvent, ketone/aldehyde molar ratio and temperature. In this procedure only cyclohexanone gave the bis-enone, by-product of the conventional aldol condensation, in low amount even at high benzaldehyde/cyclohexanone molar excess. Under the assayed conditions null or low ketol amounts were observed, except for the reaction of cyclopentanone and p-nitrobenzaldehyde. Moreover, kinetic data of BSA-catalysed aldol condensation of cyclohexanone and p-nitrobenzaldehyde suggest an ordered bi bi mechanism for enone formation; an enamine mechanism involving residues of the catalytic cavity exhibiting abnormal pKa values is also proposed.

Intraparticle Diffusional versus Site Effects on Reaction Pathways in Liquid-Phase Cross Aldol Reactions

Chemo- and regioselectivity in a heterogeneously catalyzed cross aldol reaction were directed by tuning the nature of the sites, textural properties, and reaction conditions. Catalysts included sulfonic acid-functionalized resins or SBA-15 with varying particle size or pore diameter, H-BEA zeolites, and Sn-BEA zeotype; conditions were 25 °C to 170 °C in organic media. Benzaldehyde and 2-butanone yielded branched (reaction at -CH2- of butanone) and linear (reaction at -CH3) addition and condensation products; and fission of the branched aldol led to β-methyl styrene and acetic acid. Strong acids promoted the dehydration step, and regioselectivity originated from preferred formation of the branched aldol. Both, resins and functionalized SBA-15 materials yielded predominantly the branched condensation product, unless particle morphology or temperature moved the reaction into the diffusion-limited regime, in which case more fission products were formed, corresponding to Wheeler Type II selectivity. For H-form zeolites, fission of the branched aldol competed with dehydration of the linear aldol, possibly because weaker acidity or steric restrictions prevented dehydration of the branched aldol.

Tetrahedral boronates as basic catalysts in the aldol reaction

β-Hydroxyketones are versatile building blocks in organic synthesis, which can be conveniently synthesized from ketones and aldehydes by aldol reactions. Unfortunately, these reactions often suffer from dehydration of the initially formed β-hydroxyketones

Tetranuclear BINOL-titanium complex in selective direct aldol additions

(Chemical Equation Presented) The extremely robust and water-stable tetranuclear complex Ti4(μ-BINOLato)6(μ3- OH)4 (1) catalyzes the direct aldol addition with high degrees of regioselectivity at the sterically more encumbered α-side of unsymmetrical ketones. The formation of quaternary stereocenters is described. Oxygen-containing ene components can also be used as starting material in these reactions. When used with aliphatic aldehydes, acetals 18 or acetals of aldol adducts 20 were observed. As few as 0.2 mol % loadings with this catalyst 1 were enough to complete the reactions. Mechanistical aspects of the reactions are discussed.

A catalytic aldol reaction and condensation through in situ boron "ate" complex enolate generation in water

(Chemical Equation Presented) Cooperation is key: N-Butyl-1-benzimidazole- 2-phenylboronic acid hydroxide complex catalyzes the aldol condensation and aldol addition between hydroxyacetone or acetone, and different aldehydes in water. The catalytic activity results from cooperative interactions between the boronate complex and the imidazole function. Aldol condensation gives the unsaturated methyl ketones of acetone, whereas aldol addition predominates with hydroxyacetone.

Generation of rhodium enolates via retro-aldol reaction and its application to regioselective aldol reaction

Retro-aldol reactions of β-hydroxy ketones take place under rhodium catalysis, leading to regioselective formation of the corresponding rhodium enolates. The enolates react with aldehydes in situ to afford the corresponding aldol adducts in high yields.

Highly diastereo- and enantioselective direct aldol reactions of aldehydes and ketones catalyzed by siloxyproline in the presence of water

Proline-based organocatalysts have been developed for a highly enantioselective, direct aldol reaction of aldehydes and ketones in the presence of water. While several surfactant-proline combined catalysts have proved effective, proline derivatives with a hydrophobic moiety such as rraw-siloxy-L-proline and cis-siloxy-D-proline, both of which are easily prepared from the same commercially available 4-hydroxy-L-proline. have been found to be the most effective organocatalysts examined in this study, affording the aldol product with excellent diastereo- and enantioselectivities, these two catalysts generating opposite enantiomers. Water affects the selectivity, and poor results are obtained under neat reaction conditions or in dry organic solvents. More than three equivalents of water are required for the best diastereo- and enantioselectivities. while three equivalents is the recommended amount from a synthetic point of view. The reaction proceeds in the organic phase, and also proceeds in the presence of a large amount of water. The large-scale preparation of aldols with the minimal use of an organic solvent, including in the purification step. is described.

Unusual highly regioselective direct aldol additions with a moisture-resistant and highly efficient titanium catalyst

The extremely robust and water-stable tetranuclear complex Ti 4(μ-BINOLato)6(μ3-OH)4 was found to catalyze the direct aldol addition with high regioselectivities at the more steric α-encumbered side of unsymmetr

Direct aldol and tandem Mannich reactions in room temperature ammonia solutions

An economical, simple, and efficient direct aldol reaction via the double activation of both aldehydes and ketones by ammonia has been developed. An unprecedented tandem Mannich reaction was observed when hydroxybenzaldehydes, pyrrole-2-carboxyaldehyde, a

Organometallic reactions in aqueous media - Bismuth-mediated crossed aldol type reactions

Bismuth metal, upon activation by zinc fluoride, can effect the crossed aldol reaction between α-bromocarbonyl compounds and aldehydes in aqueous media. The reaction was found to be regiospecific and syndiastereoselective.