23294-41-9

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Bis[(R)-1-phenylethyl]amine is used as an intermediate for the synthesis of chirally optically active drugs and compounds. Its application is crucial in the development of new medications with improved efficacy and reduced side effects.
Used in Synthesis of β-amino acids:
(+)-Bis[(R)-1-phenylethyl]amine is used as a starting material for the synthesis of β-amino acids, which are essential building blocks in the development of various pharmaceuticals and biologically active molecules.
Used in Preparation of Scytophycin C Moieties:
(+)-Bis[(R)-1-phenylethyl]amine is used in the preparation of chiral C(19)-C(26) and C(27)-C(32) moieties of scytophycin C, a potent anti-cancer agent. Its role in this process is to ensure the correct stereochemistry of the final product.
Used to Induce Enantioselectivity:
(+)-Bis[(R)-1-phenylethyl]amine is used to induce enantioselectivity in the deprotonation of prochiral ketones. This property is vital in the synthesis of enantiomerically pure compounds, which are essential for the development of effective drugs with minimal side effects.
Used in Synthesis of Chiral Phenolate Ligands:
(+)-Bis[(R)-1-phenylethyl]amine serves as a starting material for the synthesis of chiral phenolate ligands through the Mannich condensation reaction. These ligands are crucial in various catalytic processes and the development of new pharmaceuticals.
Used in Synthesis of Chiral Phosphoramidite Ligands:
(+)-Bis[(R)-1-phenylethyl]amine is used in the synthesis of chiral phosphoramidite ligands, which are essential in asymmetric catalysis and the development of enantiomerically pure compounds.
Used in Preparation of Chiral Cyclic Isoimidium Salts:
(+)-Bis[(R)-1-phenylethyl]amine is used to prepare chiral cyclic isoimidium salts, which are further utilized in the synthesis of chiral lactones through the Diels-Alder reaction. This application is significant in the development of complex molecular structures with specific stereochemistry, which are essential in the pharmaceutical industry.

InChI:InChI=1/C16H19N/c1-13(15-9-5-3-6-10-15)17-14(2)16-11-7-4-8-12-16/h3-14,17H,1-2H3/t13-,14-/m1/s1

Upstream product

• 40636-57-5 (αS)-α-methyl-N-(1-phenylethylidene)benzenemethanamine 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 69350-13-6 N-benzylidene-(S)-α-methylbenzylamine 
• 100483-17-8 (E)-N-<1-phenylethylidene>-1-phenylethylamine 
• 98-86-2 acetophenone 
• 676-58-4 methylmagnesium chloride 
• 618-36-0 rac-methylbenzylamine 
• 98-85-1 1-Phenylethanol 
• 40648-92-8 hydrochloride salt of (1S,1'S)-bis(1-phenylethyl)amine 
• 25102-87-8 N-(α-methyl)benzylidene 1-phenylethanamine 
• 917-54-4 methyllithium 
• 56941-77-6 (R)-1-phenylethyl(benzylidene)amine 
• 104873-95-2 [(R)-1-(4-Chloro-phenyl)-ethyl]-((R)-1-phenyl-ethyl)-amine 

Downstream Products

• 246236-70-4 (S,S)-(E)-N-cinnamoyl-bis(α-methylbenzyl)amine 
• 712352-08-4 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 
• 376355-58-7 N,N-bis-[(S)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine 
• 777067-25-1 [(S,S)-bis(α-methylbenzyl)amino]phosphorous dichloride 
• 409365-86-2 (S,S)-(-)-N,N-bis(1-phenylethyl)acrylamide 
• 712352-08-4 [(R)-1,1'-binaphthyl-2,2'-diyldioxy]{bis[(S)-(1-phenylethyl)]amino}phosphine 
• 108462-22-2 methyl (S,S)-N,N-bis(1-phenylethyl)carbamate 

Relevant academic research and scientific papers

An Iridium Catalytic System Compatible with Inorganic and Organic Nitrogen Sources for Dual Asymmetric Reductive Amination Reactions

Asymmetric reductive amination (ARA) is one of the most promising methods for the synthesis of chiral amines. Herein we report our efforts on merging two ARA reactions into a single-step transformation. Catalyzed by a complex formed from iridium and a steric hindered phosphoramidite, readily available and inexpensive aromatic ketones initially undergo the first ARA with ammonium acetate to afford primary amines, which serve as the amine sources for the second ARA, and finally provide the enantiopure C2-symmetric secondary amine products. The developed process competently enables the successive coupling of inorganic and organic nitrogen sources with ketones in the same reaction system. The Br?nsted acid additive plays multiple roles in this procedure: it accelerates the formation of imine intermediates, minimizes the inhibitory effect of N-containing species on the iridium catalyst, and reduces the primary amine side products.

Method for synthesizing chiral phosphite ligand based on R - 2 - phenylethylamine

The invention discloses a method for synthesizing chiral phosphite ligand based on R - 2 -phenylethylamine. To the method, R - 2 -phenylethylamine is reacted with acetophenone to obtain the imine intermediate, and then is mixed with H. 2 Under

One-Pot Synthesis of Symmetrical Tertiary and Secondary Amines from Carbonyl Compounds, Ammonium Carbonate and Carbon Monoxide as a Reductant

Rh-catalyzed one-step synthesis of tertiary and secondary amines from aldehydes and ketones, ammonium carbonate serving as nitrogen source, and carbon monoxide as a reducing agent has been developed. Aliphatic and aromatic aldehydes lead to the corresponding tertiary symmetrical amines in 69–83 % yields. Aromatic and aliphatic ketones lead to the corresponding secondary symmetrical amines which were obtained in 62–79 % yields.

Preparation method of chiral amine compounds

The invention discloses a preparation method of chiral amine compounds. The preparation method of the chiral amine compounds specifically comprises the following steps: adding ketone compounds and chiral auxiliary (S)-a-phenylethylamine or (R)-a-phenylethylamine to an organic solvent to prepare an imine intermediate under the action of a large-steric-hindrance boron catalyst and a water removing agent; adding a reducing agent to the imine intermediate without separation and purification, and preparing the chiral amine compounds with a one-pot method. By calculation, the product yield is 81%-96%, and the highest de value can reach 99%. Compared with the prior art, the use amount of the large-steric-hindrance boron catalyst in the method can be reduced to 0.1 mol%, use of the equivalent metal catalyst is avoided from the source, and the method has the characteristics of being simple to operate, mild in reaction condition, wide in substrate applicability, environmental friendly and the like, and has better application value and potential economic and social benefits.

B(C6F5)3-Catalyzed Asymmetric Reductive Amination of Ketones with Ammonia Borane

The first example of metal-free B(C6F5)3-catalyzed asymmetric reduction amination of ketones with chiral α-methylbenzylamine (α-MBA) using ammonia borane as the reductant is reported. This one-pot method has a broad substrate scope and provides various chiral amines in 81-95% yield with 80-99% de. This protocol was further applied in the total synthesis of cinacalcet.

Iron catalyzed diastereoselective hydrogenation of chiral imines

Cyclopentadienone-based iron complexes were used for the first time to successfully catalyze the diastereoselective hydrogenation of enantiopure imines. Chiral amines, including valuable biologically active products, were obtained often as enantiomericall

Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes

The synthesis and study of the catalytic activity of 1,2,4,3-triazaphospholenes (TAPs) is reported. TAPs represent a more modular scaffold than previously reported diazaphospholenes. TAP halides were shown to catalyze the 1,2 hydroboration of 19 imines, and three α,β unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate, a mechanism distinct from diazaphospholene catalyzed hydroborations.

Catalytic Asymmetric Reductive Condensation of N–H Imines: Synthesis of C2-Symmetric Secondary Amines

A highly diastereoselective and enantioselective Br?nsted acid catalyzed reductive condensation of N?H imines was developed. This reaction is catalyzed by a chiral disulfonimide (DSI), uses Hantzsch esters as a hydrogen source, and delivers useful C2-symmetric secondary amines.

Phosphoramidite Ligands Based on Simple 1,2-Diols: Synthesis, Use in Copper-Catalyzed Asymmetric Additions, and Achirotopic Stereogenic Phosphorus Centres

Phosphoramidite ligands are widely used in catalysis and normally constructed from large C2-symmetrical diols such as BINOL or TADDOL. We report here on new ligands based on a set of simple diols that had been previously overlooked. Ligands based on (S,S)-trans-cyclohexanediol and (R,R)-(+)-1,2-diphenyl-1,2-ethanediol, in combination with both chiral and achiral amines, were tested in 3 different copper-catalyzed asymmetric reactions and up to 89% ee was observed. A different ligand gave the best results in each reaction examined. Using meso-cis-cyclohexanediol and meso-cis-diphenyl-1,2-ethanediol with a chiral non-racemic amine gave diastereomeric ligands bearing achirotopic stereogenic phosphorus atoms which were characterized with the assistance of X-ray crystallography and variable temperature NMR studies. This work provides a new set of ligands that may be useful in some asymmetric reactions when phosphoramidites based on BINOL and TADDOL are ineffective. We also identify a novel stereochemical feature of phosphoramidites that may be useful in asymmetric catalysis and ligand design. (Figure presented.).

First efficient two-step/one-pot zirconium (IV)isopropoxide-mediated reductive amination of carbonyl compounds

An efficient method for the synthesis of various primary and secondary amines through a zirconium(IV) isopropoxide-mediated reductive amination reaction of aldehydes and ketones is reported. A series of different aldehydes, ketones and amines were used leading to the expected amino products in moderate to excellent yields. The mechanistic rationale of this reaction has been postulated through the formation of a transient imine species and a diastereoselective version using (R)-phenylethylamine as chiral inducer led to the expected products in moderate to excellent yields and with diastereoselectivities up to 100%.