185533-07-7

Upstream product

• 108-86-1 bromobenzene 
• 640-68-6 D-Val-OH 
• 108-90-7 chlorobenzene 
• 72-18-4 L-valine 

Downstream Products

• 13328-73-9 (2Ξ,4R)-4-isopropyl-2-methyl-2,3-diphenyl-[1,3,2]oxazasilolidine-5-one 

Relevant academic research and scientific papers

“On Water” promoted N-arylation reactions using Cu (0)/myo-inositol catalytic system

Myo-inositol is originally applied as a cardiovascular medicine in clinic, which can be multi-ton manufactured via extraction from the byproducts in agricultural product processing such as defatted rice bran and corn-soaking water. Herein, the application of myo-inositol (MI) as a novel versatile tridentate O-donor ligand has been first described for promoting Cu-catalyzed amination reaction in aqueous medium.

Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

Copper(ii)-catalyzed c-n coupling of aryl halides and n-nucleophiles promoted by quebrachitol or diethylene glycol

Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-Arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C-N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.

Copper-catalyzed: N -(hetero)arylation of amino acids in water

An environmentally benign, mild, cost-effective and gram-scalable copper-catalyzed method for the N-(hetero)arylation of zwitterionic natural and unnatural amino acids using 2-isobutyrylcyclohexanone as a β-diketone ligand and aryl bromides as coupling partners in water for 50 min at 90 °C under microwave irradiation is reported. Electronically and sterically diverse aryl coupling partners were inserted efficiently, including challenging heteroaryl electrophilic partners in high yields without affecting the enantiopurity of the product.

Palladium-catalyzed coupling reaction of amino acids (esters) with aryl bromides and chlorides

The bulky and electron-rich MOP type ligands and Pd(dba)2 combinations showed high efficiency for the coupling reactions of amino acids and inactive aryl halides to give N-aryl amino acids. Under the catalytic conditions, not only α-amino acids, but also β-, γ-, and δ-amino acids have been coupled with aryl chlorides in moderate to high yields; in the case of optically pure β-amino acids as substrates, the optical purities of the coupling products retained.

Copper-catalyzed aryl amination in aqueous media with 2- dimethylaminoethanol ligand

Copper-catalyzed amination of aryl bromides and iodides under mild conditions has been developed with 2-dimethylaminoethanol as ligand and water as solvent. A variety of hydrophilic and hydrophobic aryl halide substrates have been aminated in good yield with a variety of amino acids, amino alcohols and peptides. This method has successfully N-arylated some hydrophilic amino compounds not available by other methods.

Accelerating effect induced by the structure of α-amino acid in the copper-catalyzed coupling reaction of aryl halides with α-amino acids. Synthesis of benzolactam-V8

The coupling of optically pure α-amino acids with aryl halides produces enantiopure N-aryl-α-amino acids with retention of configuration under the catalysis of CuI. This reaction can complete at much lower temperature than typical Ullmann condensation even for electron-rich aryl halides, which indicates that an accelerating effect induced by the structure of the α- amino acid exists in this reaction. α-Amino acids with larger hydrophobic groups give higher coupling yields, while those with smaller hydrophobic groups only deliver lower yields and no coupling products were detected for those with hydrophilic groups. No racemization was observed in most cases of this coupling reaction. After some controlled experiments, a possible mechanism including the π-complex and the intramolecular substitution reaction is proposed. Based on this catalyzed reaction, a facile and stereoselective synthesis of benzolactam-V8, a new PKC activator, is achieved.

Synthesis of chiral N-aryl-α-amino acids by Pd-Cu catalyzed couplings of chiral α-amino acids with aryl halides

A concise synthesis of chiral N-aryl-α-amino acids, the common core structures for several biologically important molecules, by Pd-Cu catalyzed coupling of L- or D-α-amino acids and aryl halides, is described. Copyright (C) 1996 Published by Elsevier Scie