5634-59-3

Upstream product

• 22065-57-2 ethyl 2-phenyldiazoacetate 
• 106-47-8 4-chloro-aniline 
• 101-97-3 Ethyl 2-phenylethanoate 
• 19078-72-9 bromo(phenyl)acetyl chloride 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 

Downstream Products

• 33984-30-4 (4-chloro-anilino)-phenyl-acetic acid 
• 93-89-0 benzoic acid ethyl ester 

Relevant academic research and scientific papers

An efficient method to prepare sulfoxonium ylides and their reactivity studies using copper powder and Sc(III) as catalysts: Molecular and electronic structure analysis

Sulfoxonium ylides are the viable alternatives for diazo compounds as carbene precursors. Unlike diazo compounds, these are bench-stable and crystalline solids. However, the existing methods for the synthesis of sulfoxonium ylides have disadvantages related to the yields, substrate scope, and usage of expensive catalysts. Therefore, it is necessary to develop efficient and competitive protocols for the preparation of sulfoxonium ylides. In this study, we developed an economically affordable protocol for the synthesis of sulfoxonium ylides from diazo compounds using copper powder as a catalyst. This protocol leads to the efficient multigram-scale synthesis of a wide range of sulfoxonium ylides in good yields. Further, we demonstrated scandium triflate–catalyzed carbene insertion into the N?H bond from sulfoxonium ylide. A variety of anilines and sulfoxonium ylides with various functional groups reacted well and produced the corresponding α-amino esters in good yields. All the synthesized compounds were characterized using various standard spectroscopic and analytical techniques. We also used computational methods to understand the electronic structure of all the sulfoxonium ylides using geometry optimization, frequency calculation, molecular orbital and natural bond orbital analysis, and energy decomposition analysis. Our computational results revealed that the interaction between carbene and dimethyl sulfoxide is covalent in nature and stable enough to handle in the absence of any catalyst.

Metal-Free Insertion of Sulfoxonium Ylides into Arylamines in Water

Carbenoid-based N-H insertions have undergone significant development with respect to C-N bond formation in recent years. However, the existing methods suffer from unstable starting materials, expensive metal catalysts and organic solvents. Herein, insertion of sulfoxonium ylides into arylamines under metal-free conditions has been developed. The method employs water as solvent at mild temperature and is amenable to the late-stage modification of structurally complex bioactive compounds.

Phosphine ligands stabilized Cu(I) catalysts for carbene insertion into the N-H bond

Phosphine ligands have been successfully used along with Cu(I) for several catalytic reactions, nevertheless these ligands were less explored relatively for carbene involved reactions owing to the formation of carbene-phosphine ylides. In this report we successfully used three different phosphine stabilized Cu(I) complexes (1-3) as catalysts for chemoselective carbene insertion into the N-H bond of different aromatic amines over the formation of olefin (carbene dimerized product). In order to understand the substrate scope, different α-diazo esters have been reacted with large number of amines and all the reactions produced reasonably good yields under normal experimental conditions (38 examples). All the carbene inserted products have been isolated by column chromatography and fully characterized using standard spectroscopic techniques without any ambiguities. Several control reactions have been conducted in order to understand the importance of the type of phosphine ligands used in the catalysts 1-3 and found that without these catalysts we observed less selectivity (more of olefin as the product over N-H inserted product) and low yield. From this present study, it can be noted that the rigid framework phosphine ligands would be the better choice for carbene chemistry. The results obtained from the current studies would inspire chemists to develop more novel Cu(I)-phosphine catalysts for carbene related reactions including asymmetric versions in the near future.

Palladium-catalyzed carbenoid based N-H bond insertions: Application to the synthesis of chiral α-amino esters

A highly efficient palladium-catalyzed carbenoid based N-H bond insertion has been developed. The α-amino esters were obtained in high isolated yields. Moreover, by choosing a suitable chiral auxiliary, stereoselective Pd-catalyzed N-H insertion has been realized. The chiral α-amino esters were obtained in high yields (up to 91%) and with excellent diastereoselectivities (d.r. > 19:1). The Royal Society of Chemistry.

Diastereoselective reduction of α- imino esters with tris(trimethylsilyl)aluminum

Tris(trimethylsilyl)aluminum was found to be a good chemoselective reducing reagent for a-imino esters to give a-amino esters in good yields. Application to the reduction of 3,5-disubstituted 5,6-dihyro-2H-1,4-oxazine-2-ones realized a stereoselective con

N-SUBSTITUTED AMINO ACID DERIVATIVES WITH HYPERALPHALIPOPROTEINAEMIC ACTIVITY

A series of N-substituted amino acid derivatives was synthesized and the compounds were evaluated for their effects on serum total cholesterol, HDL cholesterol and triglycerides in experimental animals.Hyperalphalipoproteinaemic activity was found for some of these compounds tested, especially BRL 26314 (2) and related 3-aryl-2-aminopropionic acids.Structure-activity relationships are discussed.Keywords: N-substituted amino acid derivatives / hyperalphalipoproteinaemic activity