10557-01-4

Upstream product

• 591-51-5 phenyllithium 
• 7449-74-3 N-methyl-N-trimethylsilylacetamide 
• 17945-94-7 3-phenyl-1-azabicyclo[1.1.0]butane 
• 1564-64-3 9-Bromoanthracene 
• 5933-40-4 (R)-(+)-N,α-dimethylbenzylamine 
• 523-27-3 9,10-Dibromoanthracene 
• 118762-10-0 N-chloro-N,α-dimethylbenzylamine 
• 98-86-2 acetophenone 
• 74-89-5 methylamine 
• 142362-68-3 1,4,6,9-tetramethyl-9-phenyl-1,2,3,4,6,7,8-heptaazaspiro[4.4]nona-2,7-diene 

Downstream Products

• 42882-26-8 N-methyl-N-(1-phenylethyl)amine 
• 19131-99-8 N-methyl-N-[(S)-1-phenylethyl]amine 
• 34497-10-4 2-methyl-3-phenylisoquinolin-1(2H)-one 
• 21868-89-3 1,2,3,4-Tetrahydro-2-methyl-3-phenylisoquinolin-1-one 
• 16114-06-0 N-Methyl-N-(1-phenylethenyl)benzamide 
• 1380214-00-5 C₁₈H₁₅NO₃ 
• 1380214-01-6 C₁₈H₁₇NO₃ 
• 1379459-38-7 2-(methyl(1-phenylvinyl)carbamoyl)phenyl acetate 
• 1447822-91-4 tert-butyl N-methyl-N-(1-phenylpentyl)carbamate 
• 1447822-92-5 tert-butyl N-methyl-N-(3-methyl-1-phenylbutyl)carbamate 
• 1447822-93-6 tert-butyl N-(3,3-dimethyl-1-phenylbutyl)-N-methylcarbamate 
• 1447822-73-2 tert-butyl N-methyl-N-(1-phenylvinyl)carbamate 
• 1447822-75-4 [(1R,2R,5S)-2-isopropyl-5-methylcyclohexyl] N-methyl-N-(1-phenylvinyl)carbamate 
• 5933-40-4 (R)-(+)-N,α-dimethylbenzylamine 

Relevant academic research and scientific papers

Disulfonimides versus phosphoric acids in br?nsted acid catalysis: The effect of weak hydrogen bonds and multiple acceptors on complex structures and reactivity

In Br?nsted acid catalysis, hydrogen bonds play a crucial role for reactivity and selectivity. However, the contribution of weak hydrogen bonds or multiple acceptors has been unclear so far since it is extremely difficult to collect experimental evidence

A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines

Chloramines are an important class of reagents, providing a convenient source of chlorine or electrophilic nitrogen. However, the instability of these compounds is a problem which makes their isolation and handling difficult. To overcome these hazards, a continuous-flow approach is reported which generates and immediately reacts N-chloramines directly, avoiding purification and isolation steps. 2-Chloramines were produced from the reaction of styrenes with N-alkyl-N-sulfonyl-N-chloramines, whilst N-alkyl or N,N’-dialkyl-N-chloramines reacted with anisaldehyde in the presence of t-BuO2H oxidant to afford amides. Primary and secondary imines were produced under continuous conditions from the reaction of N-chloramines with base, with one example subsequently reduced under asymmetric conditions to produce a chiral amine in 94% ee.

Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst

A novel cationic [IrH(THF)(P,N)(imine)] [BArF] catalyst containing a P-stereogenic MaxPHOX ligand is described for the direct asymmetric hydrogenation of N-methyl and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile tetrahydrofuran ligand allows for effective activation and reactivity, even at low temperatures. Density functional theory calculations allowed the rationalization of the stereochemical course of the reaction.

Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines

A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O has been developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method tolerates a large variety of alkyl amines, thus illustrating potential for a general reductive cross-coupling of ketones with diverse amines, and it was applied in the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline. A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O was developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method was successfully applied to the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline.

Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates

N-Alkenyl ureas and N-alkenyl carbamates, like other N-acyl enamines, are typically nucleophilic at their β-carbon. However, by incorporating an α-aryl substituent, we show that they will also undergo attack at the β-carbon by organolithium nucleophiles,

Synthesis, x-ray structure and photo chemistry of 2-(methyl(1-phenylvinyl) carbamoyl)phenyl acetate

2-(Methyl(1-phenylvinyl)carbamoyl)phenyl acetate (SM), empirical formula C18H17NO3, crystallizes in the triclinic space group, P-1, with unit cell parameters α= 9.10870(10) A , b = 10.56940(10) A , c = 16.1340(2) A , a = 7

X-ray crystal structure and photo chemistry of N-methyl-N-(1-phenylvinyl) benzamide

N-methyl-N-(1-phenylvinyl)benzamide (I) has empirical formula C16H15NO, crystallizes in the monoclinic space group, P21/n, with unit cell parameters a = 8.9101(2) A , b = 15.1416(4) A , c = 9.7737(2) A , α = 90°, β = 109.3320(10)°, c = 90°, Z = 4. Interes

Asymmetric control in Diels-Alder cycloadditions of chiral 9-aminoanthracenes by relay of stereochemical information

Two approaches to the synthesis of chiral 9-amino anthracenes are described. The first, by nucleophilic addition of organolithium reagents to imines promoted by BF3·OEt2, unexpectedly provided stable aminoboranes as products. The second approach, using palladium catalysed cross coupling, was more successful for primary amines, and the key 9-(α-methylbenzylamino)anthracene subjected to cycloadditions with N-methyl maleimide and maleic anhydride. Excellent reactivity was achieved with good levels of diastereoselectivity, through a favourable combination of electrostatic and hydrogen bonding effects. Trial studies of the retro Diels-Alder reaction of these cycloadducts were also performed.

Flash vacuum thermolysis of 1-azabicyclo[1.1.0]butanes. Photoelectron spectrum of 3-phenyl-2-azabuta-1,3-diene

The reaction behaviour of 1-azabicyclo[1.1.0]butanes under flash vacuum thermolysis (FVT) conditions was studied. It has been found that the thermal rearrangement of title compounds produces unstable 2-aza-1,3-dienes. The formation of these products was established by reduction, by Diels-Alder reactions and by UV photoelectron spectroscopy. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Enantioselective hydrogenation of imines with chiral (phosphanodihydrooxazole)iridium catalysts

Cationic iridium(I) complexes of chiral phosphanodihydrooxazoles were used as catalysts for the enantioselective hydrogenation of prochiral N-alkyl and N-aryl imines. The complexes are air-stable crystalline solids that can be readily prepared and are easy to handle. The structures of two complexes were determined by X-ray analysis. For N-alkyl imines of acetophenone, enantiomeric excesses of up to 79% were obtained. Dialkyl ketimines and cyclic imines showed lower reactivity and selectivity. A remarkable dilution effect was observed for the hydrogenation of the N-phenyl imine of acetophenone: decreasing the substrate and catalyst concentration led to a significant improvement of the enantioselectivity. Thus, up to 89% ee could be achieved using 0.1 mol% of catalyst. The highest enantioselectivities were obtained in weakly coordinating solvents such as CH2C12. Additives such as halides, imides, or amines were found to poison the catalyst. Hydrogen pressures of 100 bar were usually employed, but in some cases identical results were achieved with only 1 bar H2.