56072-29-8

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 78-93-3 butanone 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 4949-44-4 ethyl propanoylacetate 
• 10191-25-0 3-oxo-valeric acid 

Downstream Products

• 54951-55-2 (E)-1-(4-nitrophenyl)pent-1-en-3-one 

Relevant academic research and scientific papers

Studies on direct stereoselective aldol reactions in aqueous media

The direct aldol reaction of 4-nitrobenzaldehyde catalyzed by NaHCO 3, with three different ketones, Zn-proline, NaHCO 3/Zn-proline, and L-proline/Zn-proline in aqueous media, was studied to explore the selectivity of this environmentally benign type of reaction. Amazingly, NaHCO3 proper was found to be an efficient catalyst for the selective synthesis of β-hydroxy ketones, showing good regio- and diastereoselectivity, with all reactions being completed within 9 h. Cyclopentanone and cyclohexanone were found to give rise to reversed diastereoisomer ratios, the syn and anti isomers being the major products, respectively - an unprecedented result. Also, the observed syn diastereoselectivity of aldol reactions catalyzed by L-proline and Zn-proline is remarkable. The corresponding condensation products 7 and 8 were characterized by 1H-NMR and single-crystal X-ray analyses. Finally, a chelate- vs. nonchelate-type transition state is proposed to account for the differential diastereoselectivities.

Catalyst-free aldol reaction in a water medium

Background: With growing interest in developing environmentally friendly reactions and atom-economic processes in recent years, the utilization of water as a solvent has attracted a great deal of attention. This is not only for its low-cost, safe and envi

Substrate selective catalytic molecular hydrogels: The role of the hydrophobic effect

A catalytic hydrogel is reported for the substrate selective direct aldol reaction of aliphatic ketones based on their hydrophobicity and on the emergence of catalytic activity only after self-assembly of the catalyst.

Antibody-catalyzed decarboxylation and aldol reactions using a primary amine molecule as a functionalized small nonprotein component

Catalytic antibody 27C1 bears binding sites for both a substrate- and a functionalized small nonprotein component in the active site. We investigated the possibility of exploiting imine and enamine intermediates using a primary amine molecule into the act

A novel simple bifunctional catalyst for the direct aldol reaction

Direct aldol reactions of aldehydes and ketones can proceed smoothly in the presence of a catalytic amount of naphthol/sodium naphtholate (5 mol%) to afford the corresponding products with yields up to 98%. Such a bifunctional catalyst is more moderate than strong acid or base employed in direct aldol reactions.

Direct asymmetric syn-aldol reactions of linear aliphatic ketones with primary amino acid-derived diamines

We have designed a novel class of chiral diamine organocatalysts based on natural primary amino acids that efficiently catalyze syn-selective aldol reactions of challenging linear ketones, such as 2-butanone, and aromatic aldehydes. In the presence of trifluoroacetic acid (TFA) as Bronsted acid and 2,4-dinitrophenol (DNP) as co-catalyst, syn-aldol products have been obtained with excellent enantioselectivities of up to> 99% ee.

Lipase-catalysed decarboxylative aldol reaction and decarboxylative Knoevenagel reaction

Acrylic resin immobilized Candida antarctica lipase B (CAL-B) is able to catalyse decarboxylative aldol reaction and decarboxylative Knoevenagel reaction with good to excellent yields.

Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes

A series of proline-based dipeptide organocatalysts with two amide units (1-16) have been developed and evaluated in the direct catalytic asymmetric aldol reactions of aldehydes with cyclohexanone. These catalysts showed good solubility in organic solvents compared with their corresponding carboxyl terminal dipeptides. The robust amide bond formation allowed structural modifications and fine tuning of catalyst properties by varying the stereo and electronic effects of the terminal amide to affect the ability of hydrogen bonding formation between the catalysts and the substrates. The reactions proceeded smoothly in high yields (up to 99%), enantioselectivities (up to 98% ee) and anti-diastereoselectivities (up to 99:1) in the presence of bifunctional organocatalyst 4 under the optimal reaction conditions.

Protonated (S)-prolinamide derivatives-water compatible organocatalysts for direct asymmetric aldol reaction

Protonated chiral (S)-prolinamide derivatives have been developed as water compatible highly efficient organocatalysts for a direct enantioselective aldol reaction. A simple protonated (S)-prolinamide organocatalyst prepared from l-proline and 3-nitroanil

A simple primary-tertiary diamine-Bronsted acid catalyst for asymmetric direct aldol reactions of linear aliphatic ketones

Compared with the well-explored enamine catalysis with secondary amines, the development of efficient enamine-based primary amine catalysts has remained as an elusive goal until recently. We present herein that a simple chiral primary-tertiary diamine 1d