21086-02-2

Upstream product

• 67-64-1 acetone 
• 780-21-2 N-(4-chlorobenzylidene)aniline 
• 106-47-8 4-chloro-aniline 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 100-52-7 benzaldehyde 
• 116-11-0 2-Methoxypropene 

Downstream Products

• 128837-98-9 (2S,4S)-4-(4-Chloro-phenylamino)-4-phenyl-butan-2-ol 
• 128837-98-9 (2R,4S)-4-(4-Chloro-phenylamino)-4-phenyl-butan-2-ol 

Relevant academic research and scientific papers

Switching diastereoselectivity of direct Mannich-type reaction of cyclic ketones by polymeric laponite nanoclay catalyst

A new polymeric laponite nanoclay heterogeneous catalytic system based on HPMC (hydroxypropyl methyl cellulose) was developed for direct Mannich-type reaction of ketones with substituted benzaldehydes and anilines to afford corresponding β-amino ketones in good to high yields. Interestingly, cyclic ketones exhibited different chemoselectivity. Cyclopentanone underwent aldol condensation to give crossed-aldol product, while cyclohexanone and cyclopentanone afforded corresponding Mannich adducts. In the case of cyclohexanone, stereoselectivity was changed depending on the nature of the substitution on benzaldehydes, in which, moderate electron-donating and electron-withdrawing groups afforded the anti isomer as major products, but strongly electron-donating substituted benzaldehydes led to syn isomer as the major Mannich adducts. Mannich reaction with cycloheptanone led to Mannich adducts with excellent syn selectivity.

Highly efficient one-pot, three-component synthesis of β-aminoketones catalyzed by Fe(O2CCF3)3

(Chemical Equation Presented) A highly efficient one-pot, three-component synthesis of β-aminoketones was demonstrated using the cost-effective, noncorrosive, and easily available Fe(O2CCF3)3 as a catalyst for the first time. The method can be employed to synthesize a wide range of target compounds and to introduce different functional groups into the β-aminoketone skeleton. Additionally, the method consistently has the advantages of good yields, short reaction time, and simply experimental workup procedure, which makes it a useful process for the synthesis of functionalized β-aminoketones. Copyright Taylor & Francis Group, LLC.

Squaric acid as an impressive organocatalyst for Michael addition in water

A simple, green, and environmentally benign protocol for squaric acid (5 mg) catalyst conjugate addition of aromatic amines and thiols to unsaturated carbonyl compounds in water in good to excellent yields is developed. The advantages of low sensitivity toward moisture and oxygen, high tolerance of different functional groups, green reaction media and efficient recyclability make this organocatalyst suitable for both laboratory and industrial scale synthesis of β-substituted carbonyls under very mild conditions.

Synthesis of β-aminoketones and construction of highly substituted 4-piperidones by mannich reaction induced by persistent radical cation salts

A Mannich reaction of imines and ketones induced by persistent radical cation salts was Investigated, and a series of Mannich bases, β-amlnoketones, were synthesized. A novel cyclization to form the 4-piperidone skeleton was achieved In a tandem process. The reaction can be rationalized as a radical cation process supported by various evidence.

Direct Mannich reaction mediated by Fe(Cp)2PF6 under solvent-free conditions

Fe(Cp)2PF6 (5 mol %) efficiently catalyzed Mannich reaction of aldehydes, anilines, and ketones under solvent-free condition to give β-amino-ketones in high yield (up to 94%) within 30 min with anti-isomer in excess. Simple experimental conditions and product isolation procedure makes this protocol potential for the development of clean and environment-friendly strategy for the synthesis of β-amino-ketones.

A novel trypsin-catalyzed three-component mannich reaction

We found that the trypsin from hog pancreas displayed high activity to promote three-component Mannich reaction of aromatic aldehydes, aromatic amines, and acetone with moderate-to-excellent yields. The reaction tolerates a great range of substrates and e

Stereoselective synthesis of β-amino ketones via direct Mannich-type reactions, catalyzed with ZrOCl2·8H2O under solvent-free conditions

At room temperature, zirconium oxychloride (ZrOCl2· 8H2O) efficiently catalyzes the direct Mannich-type reaction of a variety of in situ generated aldimines using aldehydes and anilines with ketones in a three-component reaction under solvent-free conditions. The reaction proceeds rapidly and affords the corresponding β-amino ketones in good to high yields with good to excellent stereoselectivities. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Rare Earth Metal Complexes as Water-Tolerant Lewis Acid Catalysts in Organic Synthesis

Rare earth metal triflates are stable in aqueous media and can act as Lewis acid catalysts in several carbon-carbon bond forming reactions. This article describes some of these reactions; aldol and Mannich-type reactions in aqueous solution, and Friedel-Crafts acylations and Fries rearrangement in organic solvents. The reactions proceeded smoothly in the presence of a catalytic amount of the triflate under mild conditions. Moreover, the catalysts could be recovered after the reactions were completed and could be reused.

A Novel Mannich-type Reaction in Aqueous Media. Lanthanide Triflate-catalysed Condensation of Aldehydes, Amines and Vinyl Ethers for the Synthesis of β-Amino Ketones

A novel Mannich-type reation between an aldehyde, an amine and a vinyl ether is catalysed by lanthanide triflates to afford a β-amino ketone in good yield in aqueous media.