63209-59-6

Upstream product

• 14752-72-8 1,N-Diphenylpropanimine 
• 67888-69-1 (E)-[1-phenylpropylidene]phenylamine 
• 68230-33-1 2-phenyl-2-(N-phenylamino)butanenitrile 
• 62-53-3 aniline 
• 1086238-28-9 (Z)-N-(1-Phenylpropylidene)benzenamine 
• 38512-04-8 N-benzyl(1-phenylpropylidene)amine 
• 93-55-0 1-phenyl-propan-1-one 

Downstream Products

• 1041175-43-2 (S)-N-methyl-N-phenyl-(1-phenylpropyl)amine 

Relevant academic research and scientific papers

Highly enantioselective transfer hydrogenation catalyzed by diasteromeric mixtures of axially chiral (aR,S)- and (aS,S)-Biscarbolines

The mixtures of axially chiral (aR,S)- and (aS,S)-biscarboline alcohols were firstly used as catalysts in enantioselective 1,2- and 1,4-transfer hydrogenations of ketimines and β-enamino esters, respectively. This mixed axially chiral catalysts exhibited

Catalytic Mechanism Study on the 1,2- and 1,4-Transfer Hydrogenation of Ketimines and β-Enamino Esters Catalyzed by Axially Chiral Biscarboline-Based Alcohols

Axial N-O alcohols, which have two large carboline moieties connected to the axis were synthesized and used in catalytic enantioselective 1,2- and 1,4-transfer hydrogenations of total 26 ketimines and β-enamino esters. Excellent levels of enantioselectivity ranging from 91% to 99% were achieved by using catalyst (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. Interestingly, a mixture of (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide and (aR)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide was also able to provide high enantioselectivities up to 95% that is the same as that using pure (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. A plausible catalytic mechanism was suggested and total four kinds of transition states (TS) including almost 60 TS structures were investigated using density functional theory (DFT) with different basis sets such as 6-311G(2d,p). The predicted activation energy data are consistent with the experimental results. (Figure presented.).

Synthesis and application of axially chiral biscarbolines with functional N-O and sulfone for 1,2-transfer hydrogenations of ketimines

A series of axially chiral biscarboline-based sulfones were synthesized from L-tryptophane and applied for enantioselective 1,2-transfer hydrogenations of ketimines using trichlorosilane. The catalyst 4e, which had a tertiary butyl group, exhibited a good conversion and high enantioselectivities up to 96%ee in the series of reactions.

Chiral Br?nsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1-Hydrosilatrane

The asymmetric direct reductive amination of prochiral ketones with aryl amines using 1-hydrosilatrane with a chiral Br?nsted acid catalyst is reported. This is the first known example of chiral Br?nsted acid-catalyzed asymmetric reductive amination using

P-Stereogenic and Non-P-Stereogenic Ir-MaxPHOX in the Asymmetric Hydrogenation of N -Aryl Imines. Isolation and X-ray Analysis of Imine Iridacycles

A small library of Ir-MaxPHOX catalysts has been applied to the asymmetric hydrogenation of N-aryl imines. A structure-activity analysis of the three-chiral-center MaxPHOX ligand has been performed. Using complex 1b, the hydrogenation of N-aryl imines too

Asymmetric hydrogenation of imines with chiral alkene-derived boron Lewis acids

With the aim of developing easily accessible chiral Lewis acids for asymmetric hydrogenation, a variety of binaphthyl-based chiral alkenes were prepared in one step from the corresponding diols. Using the in situ generated chiral boron Lewis acids through

NOVEL PICOLINAMIDE-CINCHONA ORGANOCATALYSTS AND DERIVATIVES

The present application describes a novel type of picolinamide-cinchona organocatalyst that allows for the successful transformation of ketimines to chiral amines with very high enantioselectivities and with the highest TOFs reported for any particular organocatalyst to date. These organocatalysts have also been immobilized to a variety of solid supports, including magneto-nanoparticles.

Novel carbohydrate-derived pyridinecarboxylic organocatalysts for the enantioselective reduction of imines with trichlorosilane

A new type of carbohydrate-derived pyridinecarboxylic organocatalyst was prepared by fine-tuning a d-glucosamine backbone at the C-2 and C-3 positions. The carbohydrate-derived pyridinecarboxylic organocatalyst was used for the enantioselective reduction of imines with trichlorosilane. The reduction proceeded in high yield (up to 93%) and with moderate enantioselectivity (up to 75%).

Chiral phosphoric-acid-catalyzed transfer hydrogenation of ethyl ketimine derivatives by using benzothiazoline

Chiral phosphoric acid catalyzed transfer hydrogenation of ketimines derived from propiophenone derivatives and reductive amination of alkyl ethyl ketone derivatives were extensively examined in the presence of two representative hydrogen donors. The exce

Synthesis of novel carbohydrate-based valine-derived formamide organocatalysts by CuAAC click chemistry and their application in asymmetric reduction of imines with trichlorosilane

Novel organocatalysts combining carbohydrate and N-formyl-l-valine derivatives were prepared by CuII-catalyzed diazo transfer and CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition CuAAC click chemistry. It was found that the carbohydrate-based valine-derived formamide organocatalyst had high catalytic activity for the asymmetric reduction of imines with trichlorosilane. The reduction can proceed at room temperature in toluene in high yield (up to 98%) and with excellent enantioselectivity (up to 94%). 'CuAAC' click chemistry is a bridge to link N-formyl-l-valine derived organocatalysts with carbohydrates.