126079-18-3

Upstream product

• 105-07-7 4-cyanobenzaldehyde 
• 616-34-2 methoxycarbonylmethylamine 
• 5680-79-5 glycine ethyl ester hydrochloride 

Downstream Products

• 126079-24-1 (2R,4S,5R)-5-(4-Cyano-phenyl)-4-ethenesulfonyl-pyrrolidine-2-carboxylic acid methyl ester 
• 126079-22-9 (3aR,5R,6aS)-5-(4-Cyano-phenyl)-1,1-dioxo-hexahydro-1λ⁶-thieno[3,2-b]pyrrole-3a-carboxylic acid methyl ester 
• 1309871-02-0 (2R,4R,5R)-4-tert-butyl 2-methyl 5-(4-cyanophenyl)-4-(hydroxymethyl)-pyrrolidine-2,4-dicarboxylate 
• 1169983-27-0 (1R,3S,3aR,6aS)-methyl 3-(4-cyanophenyl)-octahydro-4,6-dioxo-5-phenylpyrrolo[3,4-c]pyrrole-1-carboxylate 
• 1093167-95-3 (2R,3S,4R,5S)-trimethyl 5-(4-cyanophenyl)pyrrolidine-2,3,4-tricarboxylate 
• 1352713-24-6 (2R,3R,4S,5R)-dimethyl 5-(4-cyanophenyl)-3-(phenylsulfonyl)pyrrolidine-2,4-dicarboxylate 
• 1352401-91-2 methyl (2'S,3R,5'S)-1'-acetyl-2'-(4-cyanophenyl)-2-oxo-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate 
• 1574239-99-8 (1S,6R,7R,9S)-methyl 9-(4-cyanophenyl)-10-oxo-8-azabicyclo[4.3.1]deca-2,4-diene-7-carboxylate 

Relevant academic research and scientific papers

Well-Designed Phosphine-Urea Ligand for Highly Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Methacrylonitrile: A Combined Experimental and Theoretical Study

A novel chiral phosphine-urea bifunctional ligand has been developed for Cu-catalyzed asymmetric 1,3-dipolar cycloaddition of iminoesters with methacrylonitrile, a long-standing challenging substrate in asymmetric catalysis. Distortion-interaction energy analysis based on density functional theory (DFT) calculations reveals that the distortion energy plays an important role in the observed enantioselectivity, which can be attributed to the steric effect between the phosphine ligand and the dipole reactant. DFT calculations also indicate that nucleophilic addition is the enantioselectivity-determining step and hydrogen bonding between the urea moiety and methacrylonitrile assists in control of the diastereo- and enantioselectivity. By a combination of metal catalysis and organocatalysis, excellent diastereo- and enantioselectivities (up to 99:1 diastereomeric ratio, 99% enantiomeric excess) as well as good yields are achieved. A wide range of substitution patterns of both iminoester and acrylonitrile is tolerated by this catalyst system, providing access to a series of highly substituted chiral cyanopyrrolidines with up to two quaternary stereogenic centers. The synthetic utility is demonstrated by enantioselective synthesis of antitumor agent ETP69 with a pivotal nitrile pharmacophore and an all-carbon quaternary stereogenic center.

Enantioselective Mannich Reaction of Glycine Iminoesters with N-Phosphinoyl Imines: A Bifunctional Approach

A bifunctional catalytic approach for the asymmetric Mannich reaction of glycine iminoesters with N-phosphinoyl imines has been developed. By the combination of metal catalysis and organocatalysis, the vicinal two stereogenic centers were efficiently constructed, affording a wide range of syn-diamino esters in high yields with excellent enantio- and diastereoselectivities (up to >99:1 dr, 99% ee).

Multilayer graphene functionalized through thermal 1,3-dipolar cycloadditions with imino esters: A versatile platform for supported ligands in catalysis

Multilayer graphene (MLG), obtained by mild sonication of graphite in NMP or pyridine, was fully characterized via atomic force microscopy (AFM), transmission electron microscopy (TEM), Raman spectroscopy and X-ray photoemission spectroscopy (XPS). Then, it was functionalized via 1,3-dipolar cycloaddition with azomethine ylides generated by thermal 1,2-prototropy of various imino esters. The resulting MLG, containing substituted proline-based amine functions, was characterized by XPS and it showed high nitrogen loading, ranging from 0.6 to 4.2 at% depending on the imino ester used. Among these functionalized MLGs a probe sample was subjected to ester hydrolysis and used as a heterogeneous N,O-chelating ligand to coordinate iridium atomic centers. This supported complex was also characterized by XPS and its catalytic activity was tested in the hydrogen transfer reduction of acetophenone, obtaining up to 85% yield. Furthermore, this catalyst could be recycled up to four times.

Ag2CO3/CA-AA-amidphos multifunctional catalysis in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides

The new Ag2CO3/CA-AA-amidphos complexes have been demonstrated as highly efficient multifunctional catalysts in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. Under optimal conditions, highly functionalized endo-4 pyrrolidines were obtained with excellent yields (up to 99% yield) and enantioselectivities (up to 96% ee).

Cycloaddition reactions of glycine imine anions to phenylazocarboxylic esters - A new access to 1,3,5-trisubstituted 1,2,4-triazoles

Phenylazocarboxylic tert-butyl esters have recently been shown to be highly versatile building blocks due to their ability to undergo nucleophilic aromatic substitutions under mild conditions, particularly well with [18F]fluoride, and to act as precursors for aryl radicals. In this article, we now report first examples for cycloaddition reactions to phenylazocarboxylates. In a one-pot reaction with readily accessible glycine imines, a variety of highly substituted 1,2,4-triazoles could be obtained.

Highly enantioselective 1,3-dipolar cycloaddition of azomethine ylides catalyzed by AgOAc/TF-BiphamPhos

A novel and highly efficient AgOAc/TF-BiphamPhos catalytic system shows excellent reactivity, diastereo-/enantioselectivity and structural scope in asymmetric 1,3-dipolar cycloaddition of azomethine ylides, especially derived from various α-substituted α-amino acids, with N-substituted maleimides and other electron-deficient alkenes.

Cu(I)-catalyzed highly exo-selective and enantioselective [3 + 2] cycloaddition of azomethine ylides with acrylates

(Chemical Equation Presented) A novel Cu(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with acrylates has been developed. Up to 98/2 exo/endo selectivity and up to 98% enantiomeric excess have been achieved.

Bifunctional AgOAc-catalyzed asymmetric [3 + 2] cycloaddition of azomethine ylides

(Chemical Equation Presented) A bifunctional AgOAc-catalyzed asymmetric cycloaddition of azomethine ylides with electronic-deficient alkenes was developed using ferrocenyloxazoline-derived N,P ligands. The reactive metal-bound azomethine ylide dipole is formed by the deprotonation with acetate, and extra base is not necessary. The reactions proceed with high enantioselectivity. This method provides an efficient and convenient route to optically active pyrrolidine derivatives.

A convenient procedure for the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides and alkenes

(Chemical Equation Presented) Silver fluoride and cinchona alkaloids catalyze the diastereo- and enantioselective 1,3-dipolar cycloaddition between azomethine ylides, generated from N-alkylideneglycine esters, and acrylates to give the corresponding endo-adducts. Azomethine ylides derived from aromatic and aliphatic aldehydes react in a highly diastereoselective reaction with good yields and enantioselectivities of the substituted pyrrolidines.