76740-22-2

Usage

Uses

Used in Asymmetric Catalysis:
(+)-N,N'-Bis<(R)-1-phenylethyl>-1,2-ethylendiamin is used as a chiral ligand for facilitating enantioselective reactions in asymmetric catalysis. Its unique structure and chiral properties enable it to form stable complexes with metal catalysts, leading to the production of enantiomerically pure compounds.
Used in Organic Synthesis:
In the field of organic synthesis, (+)-N,N'-Bis<(R)-1-phenylethyl>-1,2-ethylendiamin is used as a chiral ligand to promote enantioselective reactions, allowing for the synthesis of chiral compounds with high selectivity and purity.
Used in Pharmaceutical Industry:
(+)-N,N'-Bis<(R)-1-phenylethyl>-1,2-ethylendiamin is used in the pharmaceutical industry for the production of chiral drugs and biologically active compounds. Its ability to facilitate enantioselective reactions makes it a valuable tool in the synthesis of enantiomerically pure pharmaceuticals, which is crucial for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Chemical Research:
Due to its unique structure and chiral properties, (+)-N,N'-Bis<(R)-1-phenylethyl>-1,2-ethylendiamin has found widespread applications in chemical research. It is used as a chiral ligand in various research projects to explore enantioselective reactions and develop new methods for the synthesis of enantiomerically pure compounds.

Upstream product

• 107-15-3 ethylenediamine 
• 98-86-2 acetophenone 
• 98-84-0 D(+)-α-methylbenzylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 107-06-2 1,2-dichloro-ethane 
• 106-93-4 ethylene dibromide 
• 129171-89-7 1,4-bis<(R)-α-methylbenzyl>-1,4-diaza-1,3-butadiene 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 138812-17-6 N,N'-bis<(S)-1-phenylethyl>ethanediimine 
• 31616-26-9 N,N'-Bis-((R)-1-phenyl-ethyl)-oxalamide 

Downstream Products

• 94682-34-5 1,4-bis-(1-phenyl-ethyl)-piperazine 
• 1370700-77-8 1,3-di(1-phenylethyl)imidazolinium chloride 
• 76706-77-9 3-Methyl-1,5-bis-(1-phenyl-ethyl)-[1,5,3]diazaphosphepane 
• 76695-23-3 N,N'-Bis-[(diphenylphosphanyl)-methyl]-N,N'-bis-(1-phenyl-ethyl)-ethane-1,2-diamine 
• 76695-24-4 N,N'-Bis-{[(4-fluoro-phenyl)-phenyl-phosphanyl]-methyl}-N,N'-bis-(1-phenyl-ethyl)-ethane-1,2-diamine 
• 76695-25-5 N,N'-Bis-{[(4-chloro-phenyl)-phenyl-phosphanyl]-methyl}-N,N'-bis-(1-phenyl-ethyl)-ethane-1,2-diamine 
• 76695-19-7 3-Cyclohexyl-1,5-bis-(1-phenyl-ethyl)-[1,5,3]diazaphosphepane 
• 71918-53-1 (+)-N,N'-Dimethyl-N,N'-bis<(R)-1-phenylethyl>-1,2-ethylendiamin 
• 945215-10-1 1,3-bis[(1R)-1-phenylethyl]-2-(2-thienyl)-1,3,2-diazaphospholane 
• 1449218-80-7 1,3-bis((R)-1-phenylethyl)-1,3,2-diazaphospholidine 2-oxide 
• 65837-86-7 2-phenyl-1,3-(S,S)-bis-(1-phenyl-ethyl)-[1,3,2]diazaphospholidine 
• 171514-20-8 2-chloro-1,3-bis[(S)-1-phenylethyl]-1,3,2-diazaphospholidine 
• 281659-65-2 1,2-bis[(S)-1-phenylethyl]-2-thioxoimidazolidine 

Relevant academic research and scientific papers

Copper-Catalyzed Propargylation of Nitroalkanes

Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N-heterocycles such as pyrroles and 2-pyrrolines.

Imidazolinium chloride salts bearing wingtip groups: Synthesis, molecular docking and metabolic enzymes inhibition

A series of symmetrical imidazolinium chloride salts bearing secondary N-alkyl substituents were synthesized in good yield by the reaction of N,N′-dialkylethane-1,2-diamines and HC(OEt)3 in the presence of NH4Cl. These salts were characterized by spectroscopic methods. All compounds were tested as enzyme inhibitory agents. These novel symmetrical imidazolinium chloride salts derivatives (3a-h) effectively inhibited the cytosolic hCA I and hCA II, BChE, α-glycosidase and AChE with Ki values in the range of 18.41–121.73 nM for hCA I, 12.50–63.12 nM for hCA II, 3.72–34.58 nM for AChE, 5.50–32.36 nM for BChE, and 94.72–364.51 nM for α-glycosidase, respectively. CA isoenzymes play a crucial roles including acid-base balance homeostasis by excreting and secreting protons (H+) due to the CO2 hydration, HCO3 ? reabsorption mechanisms, and renal NH4 + output. Also, the molecular modeling is an implementation for estimation of the binding proximity of symmetrical imidazolinium chloride salts bearing secondary wingtip groups and their inhibition mechanisms and kinetics in atomic levels at the catalytic domains.

Enantioselective Ni-Al Bimetallic Catalyzed exo -Selective C-H Cyclization of Imidazoles with Alkenes

A Ni-Al bimetallic catalyzed enantioselective C-H exo-selective cyclization of imidazoles with alkenes has been developed. A series of bi- or polycyclic imidazoles with β-stereocenter were obtained in up to 98% yield and >99% ee. The bifunctional SPO ligand-promoted bimetallic catalysis proved to be critical to this challenging stereocontrol.

Enantioselective C-H Functionalization-Addition Sequence Delivers Densely Substituted 3-Azabicyclo[3.1.0]hexanes

An enantioselective C-H functionalization route to perfluoroalkyl-containing 3-azabicyclo[3.1.0]hexanes is disclosed. A modular and bench-stable diazaphospholane ligand enables highly enantioselective Pd(0)-catalyzed cyclopropane C-H functionalization using trifluoroacetimidoyl chlorides as electrophilic partners. In turn, the resulting cyclic ketimine products react smoothly with a broad variety of nucleophiles in one-pot processes enabling the rapid and modular construction of heavily substituted pyrrolidines.

Synthesis, structure, and reaction of chiral 2-azidoimidazolinium salts: (7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate

Two chiral 2-azidoimidazolinium salts [(7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate (2) and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate (3)] were synthesized, and their structures were determined by X-ray single crystal structural analysis. Migratory amidation reaction of enol silyl ether with 3 proceeded, but good diastereoselectivity was not observed in the reaction.

Diaminophosphine oxide ligand enabled asymmetric nickel-catalyzed hydrocarbamoylations of alkenes

Chiral trivalent phosphorus species are the dominant class of ligands and the key controlling element in asymmetric homogeneous transition-metal catalysis. Here, novel chiral diaminophosphine oxide ligands are described. The arising catalyst system with nickel(0) and trimethylaluminum efficiently activates formamide C-H bonds under mild conditions providing pyrrolidones via intramolecular hydrocarbamoylation in a highly enantioselective manner with as little as 0.25% mol catalyst loading. Mechanistically, the secondary phosphine oxides behave as bridging ligands for the nickel center and the Lewis acidic organoaluminum center to give a heterobimetallic catalyst with superior reactivity.

Synthesis of chiral phosphorus reagents and their application in combination with lewis acid as a cocatalyst in morita-baylis-hillman reaction

Two novel chiral thiophosphoramides and two chiral phosphoramidites were synthesized starting from (S)-α-phenylethylamine and (R)-(+) or (S)-(-)-1,1'-Bi-2-naphthol (BINOL), respectively, and their application in combination with Lewis acid as cocatalysts in asymmetric Morita-Baylis-Hillman (MBH) reaction was investigated. Dramatic rate acceleration (the corresponding adducts were obtained in fair to excellent chemical yield within 15 min-5 h) was observed in these chiral phosphorus reagents/Lewis acid cocatalyzed MBH reaction between 4-nitrobenzaldehyde and activated alkenes, and in one case, moderate enantioselectivity was achieved (the corresponding adduct's ee value is 44%). Copyright Taylor and Francis Group, LLC.

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.

Reversal of enantioselectivity using tethered bisguanidine catalysts in the aza-Henry reaction

A series of chiral guanidines were synthesized and shown to efficiently catalyze the aza-Henry reaction. Modifications of the catalyst structure revealed important selectivity trends as well as an intriguing reversal in stereoselectivity with bisguanidine

Design, development, and scale-up of a selective meso-epoxide desymmetrization process

A pilot-plant scale desymmetrization of the cyclic meso-epoxide 4b, using a chiral lithium amide prepared from symmetrical diamine 17, was designed and implemented to provide allylic alcohol 3b in high yield and greater than 99% ee. This chiral alcohol was converted to ketone 2b, a key intermediate in a new asymmetric synthesis of LY459477. Chiral diamine 17 was prepared from a readily available chiral precursor, (R)-α-methylbenzylamine, and could be recovered from the reaction mixture and reused. Studies performed to probe the mechanism of the rearrangement reaction of epoxide 4b showed that diamine 17 provided an optimal combination of selectivity and scaleability for this process.