6337-41-3

Usage

InChI:InChI=1/C9H11NO2/c1-7(11)6-9(12)8-4-2-3-5-10-8/h2-5,9,12H,6H2,1H3

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 105902-82-7 2-(hydroxy-[2]pyridyl-methyl)-acetoacetic acid ethyl ester 
• 56-23-5 tetrachloromethane 
• 7732-18-5 water 
• 67-64-1 acetone 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 14035-54-2 1,1-diphenyl-1-hydroxy-3-butanone 
• 108-22-5 Isopropenyl acetate 
• 40614-52-6 1-pyridin-2-yl-butane-1,3-dione 

Downstream Products

• 98-98-6 2-Picolinic acid 

Relevant academic research and scientific papers

L-proline-catalyzed asymmetric direct aldol reaction of heteroaromatic aldehydes and acetone: Improvement of catalytic efficiency in ionic liquid bmim [BF4]

L-proline in bmim [BF4] ionic liquid has been successfully used as an efficient and reusable catalyst for the direct asymmetric aldol reaction of acetone with different heteroaromatic aldehydes to afford higher selectivity of the aldol products with good enantioselectivity. Copyright Taylor & Francis Group, LLC.

Copper Complexes in the Promotion of Aldol Addition to Pyridine-2-carboxaldehyde: Synthesis of Homo- and Heteroleptic Complexes and Stereoselective Double Aldol Addition

CuCl2·2H2O and Cu(ClO4)2·6H2O are able to promote aldol addition of pyridine-2-carboxaldehyde (pyca) with acetone, acetophenone, or cyclohexenone under neutral and mild conditions. The general and simple one-pot procedure for the aldol addition to Cu(II) complexes accesses novel Cu complexes with a large variety of different structural motifs, from which the aldol-addition ligand can be liberated by treatment with NH3. Neutral heteroleptic complexes in which the ligand acts as bidentate, or homoleptic cationic complexes in which the ligand acts as tridentate can be obtained depending on the copper salt used. The key step in these reactions is the coordination of pyca to copper, which increases the electrophilic character of the aldehyde, with Cu(ClO4)2 leading to a higher degree of activation than CuCl2, as predicted by DFT calculations. A regio- and stereoselective double aldol addition of pyca in the reaction of Cu(ClO4)2·6H2O with acetone leads to the formation of a dimer copper complex in which the novel double aldol addition product acts as a pentadentate ligand. A possible mechanism is discussed. The work is supported by extensive crystallographic studies.

Tandem catalysis by lipase in a vinyl acetate-mediated cross-aldol reaction

The lipase Novozym435 (0.6% w/w) was used in tandem with organocatalysts in a first vinyl/isopropenyl acetate-mediated aldol reaction. The reaction was facilitated through the lipase-catalyzed in situ generation of acetaldehyde/acetone. The important features of the present methodology include the mild and facile reaction conditions, regenerability of the lipase, comparatively high yields and minimal side product formation.

A novel DNA-catalyzed aldol reaction

A novel DNA-catalyzed aldol reaction in water has been developed. This approach will be helpful in learning the role of DNA as a catalyst in the early stage during the development of life on earth. Georg Thieme Verlag Stuttgart.

Chitosan hydrogel: A green and recyclable biopolymer catalyst for aldol and Knoevenagel reactions

Chitosan hydrogel is efficiently utilized as an organocatalyst for aldol and Knoevenagel reactions, providing the products in high yields with a high chemoselectivity under biphasic conditions. The catalyst was recovered by simple filtration and reused several times without significant loss of activity. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.

Convenient enol equivalents for catalytic aldol-transfer reactions

Solid crystalline and stable 1,1-diphenyl-1-hydroxy-3-butanone was shown to serve as an excellent precursor of the Al-enolate of acetone generated in situ for Al-BINOL catalyzed aldol-transfer reactions of aldehydes. The best yields were obtained with electron rich aromatic aldehydes and 2-pyridine carbaldehyde of which the latter gave 1-hydroxy-1-(2-pyridyl)-3-butanone in 79% yield.

Catalytic aldol-transfer reactions with Al-alkoxide trapping

Al-BINOL catalyzed aldol-transfer reactions of aldehydes with diacetonealcohol conducted with Al-alkoxide trapping gave aldol adducts in good yields. The best yields were obtained with electron-rich aromatic aldehydes (e.g., 83% yield with 3,4,5-trimethoxybenzaldehyde).

Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water

A synthetically useful pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes with ketones in water affords the aldol addition product in up to 93% yield. Electrophilicity of the aldehydes controls the course of the reaction.

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