23958-65-8

Upstream product

• 89337-62-2 tert-butyl((1-methoxy-2-methylprop-1-en-1-yl)oxy)dimethylsilane 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 100-52-7 benzaldehyde 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 
• 538-51-2 benzylidene phenylamine 
• 72658-03-8 (Z)-1-methoxy-1-(trimethylsiloxy)propene 

Downstream Products

• 1258723-89-5 3,3,5-trimethyl-6-oxo-1,2-diphenyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate 
• 1258724-10-5 N-(2,2-dimethyl-1-phenylpent-3-yn-1-yl)-N-phenylpentanamide 

Relevant academic research and scientific papers

Imino-Diels-Alder and imino-aldol reactions catalyzed by samarium diiodide

In the presence of a catalytic amount of samarium diiodide in methylene chloride, aromatic imines react with Danishefsky diene to form tetrahydropyridine-4-ones in high yields. Under the same conditions, various imino-aldol reactions afford β-amino esters or β-amino ketones.

Solvent-free imino-aldol three-component couplings on a conveniently-prepared and reusable phosphoric acid-silica gel support

A new solvent-free procedure for the synthesis of β-amino carbonyl compounds in generally moderate to excellent yields has been developed. Three-component Mannich-type couplings between aldehydes (aromatic, aliphatic, alicyclic, and heterocyclic), aromatic amines and silyl enol equivalents proceeded smoothly on a conveniently prepared and reusable phosphoric acid-silica gel solid support.

Chemoselective activation of aldimine in preference to aldehyde by the combination of BF3?OEt2 and water: Novel catalyst for the mannich-type reaction

Reported herein are that catalytic amount of conventional Lewis acids activated aldimines in preference to aldehydes, and addition of water to BF3?OEt2 accelerated the Mannich-type reaction significantly to afford β-amino carbonyl compounds in high yields.

Mannich-type reactions in water using a hydrophobic polymer-supported sulfonic acid catalyst

Three-component Mannich-type reactions were efficiently catalyzed by hydrophobic polystyrene-supported sulfonic acid (PS-SO3H) in water as the sole solvent under mild conditions.

TTMPP catalyzed one-pot silyl ketene acetal-imine condensation route to β-lactams

Highly nucleophilic phosphine, tris(2,4,6-trimethoxy phenyl) phosphine (TTMPP) catalyzes a unique one-pot cyclization reaction between silyl ketene acetal and aldimine, resulting in β-lactam. Copyright

Mannich-type reaction of (1-methoxy-2-methylpropenyloxy)trimethylsilane with arylaldehydes and aromatic amines catalyzed by perfluorinated rare earth metal salts in fluorous phase

In this paper, we describe a useful Mannich-type reaction in fluorous phase. By use of perfluorodecalin (C10F18, cis- and trans-mixture) as a fluorous solvent and perfluorinated rare earth metal salts such as Sc(OSO2C

Strong Lewis acid air-stable cationic titanocene perfluoroalkyl(aryl) sulfonate complexes as highly efficient and recyclable catalysts for C-C bond forming reactions

A series of strong Lewis acid air-stable titanocene perfluoroalkyl(aryl) sulfonate complexes Cp2Ti(OH2)2(OSO 2X)2·THF (X = C8F17, 1·THF; X = C4F9, 2·H2O· THF; X = C6F5, 3) were successfully synthesized by the treatment of Cp2TiCl2 with C8F 17SO3Ag, C4F9SO3Ag and C6F5SO3Ag, respectively. In contrast to well-known titanocene bis(triflate), these complexes showed no change in open air over three months. TG-DSC analysis showed that 1·THF, 2·H 2O·THF and 3 were thermally stable at 230 °C, 220°C and 280°C, respectively. Conductivity measurements showed that these complexes underwent ionic dissociation in CH3CN solution. X-ray analysis results confirmed that 2·H2O·THF and 3 were cationic. ESR spectra showed that the Lewis acidity of 1·THF (1.06 eV) was higher than that of Sc3+ (1.00 eV) and Y3+ (0.85 eV). UV/Vis spectra showed a significant red shift due to the strong complex formation between 10-methylacridone and 2·H2O·THF. Fluorescence spectra showed that the Lewis acidity of 2 (λem = 477 nm) was higher than that of Sc3+ (λem = 474 nm). These complexes showed high catalytic ability in various carbon-carbon bond forming reactions. Moreover, they show good reusability. Compared with 1·THF, 2·H2O·THF and 3 exhibit higher solubility and better catalytic activity, and will find broad applications in organic synthesis. This journal is the Partner Organisations 2014.

Stereodefined homopropargyl amines by tandem nucleophilic addition/fragmentation of dihydropyridone triflates

Dihydropyridone (DHPD) triflates undergo nucleophile-triggered fragmentation to provide homopropargyl amine derivatives, the stereochemistry of which is defined by starting from readily available β-amino esters.

Cationic iridium complex is a new and efficient Lewis acid catalyst for aldol and Mannich reactions

A cationic iridium complex [Ir(cod)2]SbF6 was found to be a new and efficient Lewis acid catalyst for Mukaiyama aldol and Mannich reactions. Aldehydes react smoothly with silyl enol ethers to give β-siloxy ketones in the presence of 0.5 mol % of [Ir(cod)2]SbF6. The reaction of N-alkyl arylaldimines with ketene silyl acetals in the presence of 5 mol % [Ir(cod)2]SbF6/P(OPh)3 gave β-amino esters. After Mannich reaction was complete, stirring of the reaction mixture for 24 h led to cyclization to give β-lactam. The reaction of N-aryl benzaldimine with silyl enol ether derived from acetophenone gave a tetrahydroquinoline derivative as a single diastereomer.

Sustainable synthetic methods: Domino construction of dihydropyridin-4-ones and β-amino esters in aqueous ethanol

(Chemical Equation Presented) Domino reactions were designed to allow the byproduct of an upstream reaction to be internally recycled to catalyze a downstream reaction in a one-pot tandem sequence. Nitroarene reduction by In0 generates an amine and InIII byproducts. Addition of aldehyde followed by Danishefsky's diene or silyl ketene acetal provides access to dihydropyridin-4-ones or β-amino esters, respectively, in yields that are comparable or superior to the reported stepwise reactions.