286392-28-7

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 5680-79-5 glycine ethyl ester hydrochloride 

Downstream Products

• 1166397-81-4 trimethyl (2R,3S,4R,5S)-5-(4-trifluoromethylphenyl)pyrrolidine-2,3,4-tricarboxylate 
• 1241941-54-7 methyl 4-(2,2,2-trifluoroacetyl)-5-(4-(trifluoromethyl)phenyl)-1H-pyrrole-2-carboxylate 
• 1250954-39-2 C₂₆H₂₁F₃N₂O₃ 
• 1257079-55-2 methyl (1S,3R,3aS,6aR)-3-[4-(trifluoromethyl)phenyl]-octahydro-4-oxocyclopenta[c]pyrrole-carboxylate 
• 1309923-05-4 (2R,5R)-4,4-diethyl 2-methyl 3-(2,2-diphenylvinylidene)-5-(4-(trifluoromethyl)phenyl)pyrrolidine-2,4,4-tricarboxylate 
• 1352401-92-3 methyl (2'S,3R,5'S)-1'-acetyl-2-oxo-2'-[4-(trifluoromethyl)phenyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate 
• 1330181-98-0 dimethyl (2R,4S,5S)-5-(4-trifluoromethylphenyl)pyrrolidine-2,4-dicarboxylate 
• 1384291-19-3 (2R,3R,4S,5S)-4-ethyl 2-methyl 3-(trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pyrrolidine-2,4-dicarboxylate 
• 1417912-36-7 (2R,4S,5R)-dimethyl 4-fluoro-5-(4-(trifluoromethyl)-phenyl)pyrrolidine-2,4-dicarboxylate 
• 1422053-71-1 (1S,3R,7aS)-methyl 4,4-dimethyl-1-(4-(trifluoromethyl)phenyl)-2,3,4,7a-tetrahydro-1H-cyclopenta[c]pyridine-3-carboxylate 

Relevant academic research and scientific papers

Asymmetric construction of 3-vinylidene-pyrrolidine derivatives containing allene moiety via Ag(i)/TF-BiphamPhos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with diethyl 2-(3,3-diphenylpropa-1,2-dienylidene) malonate

Catalytic asymmetric 1,3-dipolar cycloaddition of various azomethine ylides with diethyl 2-(3,3-diphenylpropa-1,2-dienylidene)malonate has been developed successfully with good to excellent enantioselectivity for the effcient construction of 3-vinylidene-pyrrolidine derivatives containing a unique allene moiety.

Boron Dipyrromethene (BODIPY) as Electron-Withdrawing Group in Asymmetric Copper-Catalyzed [3+2] Cycloadditions for the Synthesis of Pyrrolidine-Based Biological Sensors

In this work, we describe the use of Boron Dipyrromethene (BODIPY) as electron-withdrawing group for activation of double bonds in asymmetric copper-catalyzed [3+2] cycloaddition reactions with azomethine ylides. The reactions take place under smooth conditions and with high enantiomeric excess for a large number of different substituents, pointing out the high activation of the alkene by using a boron dipyrromethene as electron-withdrawing group. Experimental, theoretical studies and comparison with other common electron-withdrawing groups in asymmetric copper-catalyzed [3+2] cycloadditions show the reasons of the different reactivity of the boron dipyrromethene derivatives, which can be exploited as a useful activating group in asymmetric catalysis. Additional experiments show that the so obtained pyrrolidines can be employed as biocompatible biosensors, which can be located in the endosomal compartments and do not present toxicity in three cell lines. (Figure presented.).

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.

Synthesis of Azacyclic Nucleoside Analogues via Asymmetric [3 + 2] Cycloaddition of 9-(2-Tosylvinyl)-9H -purines

With 9-(2-tosylvinyl)-9H-purines as the dipolarophiles, a series of chiral azacyclic nucleosides with four continuous stereocenters were obtained in 86-99% yields, >20:1 dr, and 94 → 99% ee via the Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition. Both (E)- and (Z)-9-(2-tosylvinyl)-9H-purines were suitable dipolarophiles, enriching the structure diversity of azacyclic nucleosides. Furthermore, when α-methyl imino ester was explored, the corresponding azacyclic nucleoside with a chiral quaternary stereocenter could also be afforded with excellent results. (Chemical Equation Presented).

Enantiodivergent Combination of Natural Product Scaffolds Enabled by Catalytic Enantioselective Cycloaddition

An efficient strategy has been established for the enantiodivergent synthesis of natural product inspired compounds embodying both tropane and pyrrolidine natural product fragments. This strategy includes the enantioselective kinetic resolution of racemic tropanes by means of a copper(I)-catalyzed [3+2] cycloaddition and allows the preparation of two enantiopure products in a one-pot reaction in high yield and with high diastereo- and enantioselectivity by using one chiral catalyst.

A rapid and divergent access to chiral azacyclic nucleoside analogues via highly enantioselective 1,3-dipolar cycloaddition of β-nucleobase substituted acrylates

A rapid and divergent access to chiral azacyclic nucleoside analogues has been established via highly exo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylides with β-nucleobase substituted acrylates. Using 1 mol% of a chiral copper complex, various chiral azacyclic nucleoside analogues were obtained in high yields, excellent exo-selectivities and enantioselectivities (98 to >99% ee). This journal is