19302-34-2

Upstream product

• 160718-79-6 (S)-(-)-N-butyl-N-(1-phenylethyl)allylamine 
• 6907-75-1 N-(1-phenylethylidene)butylamine 
• 109-65-9 1-bromo-butane 
• 2627-86-3 (-)-α-methylbenzylamine 
• 98-86-2 acetophenone 
• 27482-95-7 (S)-n-butylidene-α-methylbenzylamine 
• 79919-40-7 N-(1-phenylethyl)butyramide 
• 5412-64-6 butyl-(1-phenyl-ethyl)-amine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1344918-70-2 (S)-N-(2-butynyl)-(1-phenylethyl)amine 
• 115914-08-4 (S)-N-(1-phenylethyl)prop-2-en-1-amine 
• 142968-05-6 butyl(1-phenylethylidene)amine 

Relevant academic research and scientific papers

Enantioselective reduction of: N -alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions

Enantioselective reduction of ketimines was demonstrated using chiral N-heterocyclic carbene (NHC)-stabilised borenium ions in frustrated Lewis pair catalysis. High levels of enantioselectivity were achieved for substrates featuring secondary N-alkyl substituents. Comparative reactivity and mechanistic studies identify key determinants required to achieve useful enantioselectivity and represent a step forward in the further development of enantioselective FLP methodologies.

Enantioselective Formation of 2-Azetidinones by Ring-Assisted Cyclization of Interlocked N-(α-Methyl)benzyl Fumaramides

The synthesis of optically active interlocked and non-interlocked 2-azetidinones by intramolecular cyclization of N-(α-methyl)benzyl fumaramide [2]rotaxanes is described. Two different strategies of asymmetric induction were tested in which the chiral gro

Liquid chromatographic resolution of fendiline and its analogues on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid

Fendiline, an effective anti-anginal drug for the treatment of coronary heart diseases, and its sixteen analogues were resolved on a CSP based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. Fendiline was resolved quite well with the separation factor (α) of 1.25 and resolution (RS ) of 1.55 when a mobile phase consisting of methanol-acetonitrile-trifluoroacetic acid-triethylamine at a ratio of 80/20/0.1/0.5 (v/v/v/v) was used. The comparison of the chromatographic behaviors for the resolution of fendiline and its analogues indicated that the 3,3-diphenylpropyl group bonded to the secondary amino group of fendiline is important in the chiral recognition and the difference in the steric bulkiness between the phenyl group and the methyl group at the chiral center of fendiline is also important in the chiral recognition.

Asymmetric domino aza-michael addition/[3 + 2] cycloaddition reactions as a versatile approach to α,β,γ-triamino acid derivatives

Nonproteinogenic amino acids are prepared by an unprecedented domino aza-Michael addition-1,3-dipolar cycloaddition, leading to enantiopure highly substituted pyrrolidinopyrazolines. Nonaflyl azide serves as highly effective diazo transfer reagent, forming the link between the conjugate addition and cycloaddition steps. The resulting pyrrolidinopyrazolines can be rapidly transformed to either α,β,γ-triamino acids or 3,4-methano-β-prolines. Peptide coupling can be regioselectively conducted at each of the amino groups.

1,1′-Binaphthyldiamine-based lewis bases as readily available and efficient grganocatalysts for the reduction of N-Aryl and N-Alkyl ketimines

The development of simple, low-cost, efficient, and sustainable routes to enantiomerically pure amines is a topic of extraordinary interest, specially in view of future industrial applications. In this context, we wish to report a chemical and stereochemical efficient synthesis of chiral amines through the Lewis base activated trichlorosilane reduction of ketimines. An organocatalyst, easily prepared in a single step through the condensation of picolinic acid and commercially available 1,1′-binaphthyldiamine, is the key element of this metal-free methodology, that allowed the synthesis of chiral secondary and primary amines in high yields and stereose-lectivity. Noteworthy, such catalysts are able to promote the reduction of N-alkyl ketimines, often in quantitative yield and up to 87% enantioselectivity; it: is worth mentioning that for such transformations only one other organocatalytic system has been reported so far.

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.

?-Allyl palladium methodology for selective deprotection of allylamines. Practical synthesis of secondary amines

The palladium-promoted deallylation of allylamines derived from primary and secondary amines is achieved with high to quantitative yield in the presence of 2-mercaptobenzoic acid as an allyl scavenger.This method was used for the sequential cleavage of diallylamines.A synthetic application of this procedure is presented in the preparation of secondary amines from diallylamines. - Keywords: allylamine; deallylation; sequential deprotection; ?-allyl palladium complexes; 2-mercaptobenzoic acid; substitution of amines