1092456-76-2

Upstream product

• 62-53-3 aniline 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 94-41-7 benzalacetophenone 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 742-43-8 1,3-diphenyl-3-(N-phenylamino)propanone 

Relevant academic research and scientific papers

Organocatalytic aza-Michael/retro-aza-Michael reaction: Pronounced chirality amplification in aza-Michael reaction and racemization via retro-aza-Michael reaction

A detailed experimental investigation of an aza-Michael reaction of aniline and chalcone is presented. A series of Cinchona alkaloid-derived organocatalysts with different functional groups were prepared and used in the aza-Michael and retro-aza-Michael reaction. There was an interesting finding that a complete reversal of stereoselectivity when a benzoyl group was introduced to the cinchonine and cinchonidine. The chirality amplification vs. time proceeds in the quinine-derived organocatalyst containing silicon-based bulky group, QN-TBS, -catalyzed aza-Michael reaction under solvent-free conditions. In addition, we have demonstrated for the first time that racemization was occurred in suitable solvents under mild conditions due to retro-aza-Michael reaction of the Michael adduct of aniline with chalcone. These indicate the equilibrium of retro-aza-Michael reaction and aza-Michael reaction produce the happening of chirality amplification in aza-Michael reaction and racemization via retro-aza-Michael reaction under different conditions, which would be beneficial to the development of novel chiral catalysts for the aza-Michael reactions.

Screening approach for Chiral separation of β-aminoketones by HPLC on various polysaccharide-based Chiral stationary phases

Nine β-aminoketones were synthesized via Mannich reaction when benzaldehyde was condensed with some primary amines and acetophenone. The purified compounds were identified by using spectroscopic methods. The enantiomeric separation of these derivatives was carried out by high-performance liquid chromatography (HPLC) using several coated and immobilized polysaccharide stationary phases, namely, Chiralcel OD-H, Chiralcel OD, Chiralcel OJ, Chiralpak AD, Chiralpak IA, and Chiralpak IB using different mobile phases composed of n-hexane and alcohol mixed in various ratios or pure ethanol or isopropanol. The retention behavior and selectivity of these chiral stationary phases were examined in isocratic normal phase mode. The results indicate that cellulose derivatives have higher enantioselectivity than amylose derivatives for the separation of racemic β-amino ketones. Chirality 27:332-338, 2015.

Synthesis and bifunctional asymmetric organocatalysis of helical poly(phenylacetylene)s bearing cinchona alkaloid pendants via a sulfonamide linkage

Four novel helical poly(phenylacetylene)s with amino-functionalized cinchona alkaloid pendant groups connecting to the phenyl rings through a sulfonamide linkage were synthesized by the polymerization of the corresponding phenylacetylene monomers using Rh

Diaryliodonium salts as efficient Lewis acid catalysts for direct three component Mannich reactions

Diaryliodonium(iii) salts, as highly active and versatile Lewis acid catalysts for the direct three component Mannich reaction under solvent free conditions, have been investigated. The Mannich products were isolated in good to excellent yields in a very clean manner. Additionally, the catalyst could be recycled without significant loss of its catalytic activity. This journal is

Ionic amino acids: Application as organocatalysts in the aza-Michael reaction

The ethyl methyl imidazolium salts of amino acids, [emim][AA], have been used as catalysts in the aza-Michael reaction. Furthermore, when chiral amino acids were used, a stereoselective reaction was achieved. The mechanism of the transformation was verified by the detection of a key intermediate by electrospray ionization mass spectroscopy (ESI-MS).

Silicon-based lewis acid assisted cinchona alkaloid catalysis: Highly enantioselective aza-michael reaction under solvent-free conditions

The study showed that a combination of an achiral silicon-based Lewis acid and chiral Lewis base, such as iodotrimethylsilane (TMSI) and cinchonine, generated a highly enantioselective catalyst system under solvent-free conditions which gave aromatic β-amino ketones with up to >99% ee. Mechanistic studies demonstrate the enhanced asymmetric induction may be due to the combined and competitive activation of acarbonyl moiety of chalcone with cinchonine and the silicon-based Lewis acid in the aza-Michael reaction.2011 American Chemical Society.

Organocatalytic asymmetric aza-Michael addition of aniline to chalcones under solvent-free conditions

The first enantioselective Michael addition of aniline to chalcones was promoted by cheap and commercially available chincona alkaloids under solvent-free conditions. Variously substituted chalcones were examined as substrates giving the conjugate adducts