221226-19-3

Usage

Chiral diamine compound

The compound has a chiral center, which means it can exist in two different forms (enantiomers) that are non-superimposable mirror images of each other.

Use as a ligand

1R,2R-N,N'-bis(phenylMethyl)-1,2-diphenyl-1,2-EthanediaMine is commonly used to bind to metal ions in asymmetric catalysis and organic synthesis.

Efficient catalysis

1R,2R-N,N'-bis(phenylMethyl)-1,2-diphenyl-1,2-EthanediaMine is known for its ability to efficiently catalyze various chemical reactions, such as asymmetric hydrogenation and cross-coupling reactions.

Formation of chiral products

The catalyzed reactions lead to the formation of chiral products with high enantioselectivity, which is crucial for the development of pharmaceuticals and other fine chemicals.

Unique structure

The specific arrangement of phenyl and methyl groups in the compound contributes to its unique structure and properties.

Valuable tool in pharmaceutical development

Due to its ability to produce chiral products with high enantioselectivity, 1R,2R-N,N'-bis(phenylMethyl)-1,2-diphenyl-1,2-EthanediaMine is a valuable tool in the development of new pharmaceuticals and other fine chemicals.

Potential applications in material science and nanotechnology

The compound's unique properties have also attracted interest in the fields of material science and nanotechnology for potential applications in these areas.

Upstream product

• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 
• 100-44-7 benzyl chloride 
• 484001-72-1 (4R,5R)-2,2-dimethyl-4,5-diphenylimidazolidine 
• 780-25-6 N-benzylidene benzylamine 

Downstream Products

• 138421-41-7 (4R,5R)-1,2,3-Tribenzyl-4,5-diphenyl-[1,3,2]diazaphospholidine 2-oxide 
• 138421-34-8 (4R,5R)-1,3-Dibenzyl-4,5-diphenyl-[1,3,2]diazaphospholidine 2-oxide 
• 138421-29-1 (4R,5R)-1,3-Dibenzyl-2-chloro-4,5-diphenyl-[1,3,2]diazaphospholidine 

Relevant academic research and scientific papers

Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates

Siliranes undergo stereoselective and regioselective insertions of benzaldehyde to provide oxasilacyclopentane products. The thermal reaction (>100°C) leads to more decomposition and side products, whereas the catalyzed variant (t-BuOK, 95%). Treatment of siliranes with enolizable aldehydes leads to silyl enol ethers. The reaction of a silirane at high temperatures with an imine leads to reductive dimerization, presumably by way of intermediate-free silylene. The mechanism for the catalyzed insertion of benzaldehyde is discussed.

Zinc Acetate Catalyzed Enantioselective Reductive Aldol Reaction of Ketones

A highly enantioselective method for the synthesis of β-hydroxy esters via reductive aldol reaction of acrylates with aryl and heteroaromatic ketones is described. In situ generated catalyst composed of zinc acetate and chiral diamine afforded enantioenri

Nitroalkenes in the Ni(II) Catalyzed Asymmetric Michael Addition. Convenient Route to the Key Intermediate of Brivaracetam

A series of Ni(II) complexes with novel chiral ligands derived from (1R,2R)-1,2-diphenylethane-1,2-diamine was synthesized. The catalytic activity of these complexes in the asymmetric Michael reaction is demonstrated. Asymmetric addition of diethyl malonate to ω-nitrostyrene and 1-nitropent-1-ene in the presence of these complexes leads to the enantiomerically enriched diethyl (S)-2-(2-nitro-1-phenylethyl)malonate (up to 96 % ee) and (R)-diethyl 2-(1-nitropenthan-2-yl)malonate (up to 91 % ee). (4R)-4-Propylpyrrolidin-2-one, the key intermediate of antiepileptic drug brivaracetam, was obtained from the corresponding nitroester.

Enantioselective Hydrosilylation of Imines Catalyzed by Chiral Zinc Acetate Complexes

A series of zinc acetate complexes with optically pure diphenylethanediamine (DPEDA)-derived ligands have been employed as enantioselective catalyst for the hydrosilylation of various imines. High control of stereoselectivity (up to 97% ee) and excellent yields (up to 96%) were gained for a broad range of N-phosphinoylimines by using (R,R)-N,N′-dibenzyl-1,2-diphenylethane-1,2-diamine. This is the first successful application of an air-stable and environmentally friendly chiral Zn(OAc)2 complex instead of the previously used harmful diethylzinc in the asymmetric reduction of the C=N double bond.

Zinc Acetate-Catalyzed Enantioselective Hydrosilylation of Ketones

Zinc acetate complexes with a chiral diphenylethylenediamine (DPEDA)-derived ligand have been proved to be efficient catalysts for the enantioselective hydrosilylation of aryl ketones. Replacing pyrophoric dialkylzinc with the readily available zinc salt simplifies the procedures and provides excellent conversions (up to >99%) and enantioselectivities (ees up to 97%).

Catalytic, asymmetric Mannich-type reactions of N-acylimino esters: Reactivity, diastereo- and enantioselectivity, and application to synthesis of N-acylated amino acid derivatives

In the presence of a catalytic amount of Cu(OTf)2-chiral diamine 3e complex, N-acylimino esters reacted with silyl enol ethers to afford the corresponding Mannich-type adducts in high yields with high enantioselectivities. A wide variety of silyl enol ethers derived from ketones, as well as esters and thioesters, reacted smoothly. In the reactions of α-substituted silyl enol ethers (α-methyl or benzyloxy), the desired syn-adducts were obtained in high yields with high diastereo- and enantioselectivities. Several intermediates for the synthesis of biologically important compounds were prepared using this novel catalytic asymmetric Mannich-type reaction, and at the same time, absolute and relative stereochemical assignments were made. In addition, it has been revealed that alkyl vinyl ethers reacted with N-acylimino esters in the presence of a catalytic amount of the Cu(II) catalyst to give the corresponding Mannich-type adducts in high yields with high enantioselectivities. This is the first example of catalytic asymmetric Mannich-type reactions with alkyl vinyl ethers. The reaction mechanism, structure of chiral catalyst-electrophile complexes, and transition states of these catalytic asymmetric reactions were assumed based on X-ray crystallographic analysis of the Cu(II)-chiral amine complex, PM3 calculations, and FT-IR analyses, etc. Finally, (1R,3R)-N-(3-hydroxy- 1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12, 1), a new inhibitor of ceramide trafficking from endoplasmic reticulum to the site of sphingomyerin (SM) synthesis, has been synthesized efficiently using the present Mannich-type reaction as a key step. The synthesis involved three steps (two-pot), and total yield was 82.9%.