160191-71-9

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 104-94-9 4-methoxy-aniline 
• 917-54-4 methyllithium 
• 151918-10-4 3-phenylpropanal N-(4-methoxyphenyl)imine 
• 16520-62-0 4-Phenyl-1-butyne 
• 2344-70-9 1-phenyl-3-butanol 
• 324025-11-8 N-(4-methoxyphenyl)-4-phenyl-2-butylamine 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 937-52-0 (R)-1-methyl-3-phenylpropylamine 
• 1311486-17-5 C₁₇H₁₉NO 
• 104-53-0 3-phenyl-propionaldehyde 
• 160191-67-3 3-phenylpropanal (p-methoxyphenyl)imine 

Downstream Products

• 1118755-40-0 C₁₉H₂₃NO₃ 
• 101507-06-6 tert-butyl (R)-(4-phenylbutan-2-yl)carbamate 
• 937-52-0 (R)-1-methyl-3-phenylpropylamine 

Relevant academic research and scientific papers

Enantioselective organocatalytic reductive amination

The first enantioselective organocatalytic reductive amination reaction has been accomplished. The development of a new chiral phosphoric acid catalyst has provided a convenient strategy for the enantioselective construction of protected primary amines an

Chiral cyclometalated iridium complexes for asymmetric reduction reactions

A series of chiral cyclometalated iridium complexes have been synthesised by cyclometalating chiral 2-aryl-oxazoline and imidazoline ligands with [Cp?IrCl2]2. These iridacycles were studied for asymmetric transfer hydrogenation reactions with formic acid as the hydrogen source and were found to display various activities and enantioselectivities, with the most effective ones affording up to 63% ee in the asymmetric reductive amination of ketones and 77% ee in the reduction of pyridinium ions. This journal is

Nucleophilic Aromatic Substitution of Unactivated Aryl Fluorides with Primary Aliphatic Amines by Organic Photoredox Catalysis

In this work, a mild and transition-metal-free approach for the nucleophilic aromatic substitution (SNAr) of unactivated fluoroarenes with primary aliphatic amines to form aromatic amines is reported. This reaction is facilitated by the formati

Oxidative Kinetic Resolution of Acyclic Amines Based on Equilibrium Control

An oxidative kinetic resolution of racemic acyclic amines was developed using an imine derivative as the resolving reagent and chiral phosphoric acid as the catalyst to give enantiomers in good yields with high to excellent enantioselectivities. The key t

Catalytic enantioselective amination of alcohols by the use of borrowing hydrogen methodology: Cooperative catalysis by iridium and a chiral phosphoric acid

The catalytic asymmetric reduction of ketimines has been explored extensively for the synthesis of chiral amines, with reductants ranging from Hantzsch esters, silanes, and formic acid to H2 gas. Alternatively, the amination of alcohols by the use of borrowing hydrogen methodology has proven a highly atom economical and green method for the production of amines without an external reductant, as the alcohol substrate serves as the H2 donor. A catalytic enantioselective variant of this process for the synthesis of chiral amines, however, was not known. We have examined various transition- metal complexes supported by chiral ligands known for asymmetriC-Hydrogenation reactions, in combination with chiral Bronsted acids, which proved essential for the formation of the imine intermediate and the transfer-hydrogenation step. Our studies led to an asymmetric amination of alcohols to provide access to a wide range of chiral amines with good to excellent enantioselectivity.

Cooperative catalysis with iron and a chiral bronsted acid for asymmetric reductive amination of ketones

The direct asymmetric reductive amination (DARA) of ketones with anilines is described by combining a chiral Bronsted acid (TRIP) and the non-chiral Knlker iron complex as the catalyst system. In situ-formed imines are reduced with molecular hydrogen to g

Asymmetric transfer hydrogenation of ketimines by indoline as recyclable hydrogen donor

(Chemical Equation Presented) The chiral phosphoric acid catalyzed enantioselective transfer hydrogenation of various ketimines was achieved by the use of 2-aryl indoline as the hydrogen donor. Corresponding chiral amines were obtained in good chemical yi

Consecutive intermolecular reductive hydroamination: Cooperative transition-metal and chiral Br?nsted acid catalysis

Enantiomerically pure chiral amines are of increasing importance and commercial value in the fine chemical, pharmaceutical, and agrochemical industries. Here, we describe the straightforward synthesis of chiral amines by combining the atom-economic and environmentally friendly hydroamination of alkynes with an enantioselective hydrogenation of in situ generated imines by using inexpensive hydrogen. By following this novel approach, a wide range of terminal alkynes can be reductively hydroaminated with primary amines including alkyl-, and arylalkynes as well as aryl and heteroaryl amines. Excellent yields and selectivities up to 94 % ee and 96 % isolated yield were obtained.

Enantioselective organocatalytic reductive amination of aliphatic ketones by benzothiazoline as hydrogen donor

The chiral phosphoric acid-catalyzed enantioselective reductive amination of aliphatic ketones with aromatic amines was successfully achieved by the use of benzothiazoline as the hydrogen donor. Corresponding chiral aliphatic amines were obtained with exc

Scope of the organocatalysed asymmetric reductive amination of ketones with trichlorosilane

A highly active organocatalyst has been shown to affect the asymmetric reductive amination of ketones producing both aromatic and aliphatic amines. At 1 mol% catalyst loading, a series of structurally diverse chiral amines were quickly and economically prepared with good enantioselectivity and generally useful yield. The efficient synthesis of the calcimimetic (+)-NPS R-568 (67%, 89% ee) demonstrated the synthetic applicability of this methodology.