334651-13-7

Upstream product

• 14019-62-6 glycine isopropyl ester hydrochloride 
• 100-52-7 benzaldehyde 
• 13048-66-3 glycine isopropyl ester 

Downstream Products

• 1062148-58-6 4-tert-butyl 2-isopropyl (2S,4S,5R)-5-phenyl-2,4-pyrrolidinedicarboxylate 
• 1062148-60-0 4-tert-butyl 2-isopropyl (2R,4R,5S)-5-phenyl-2,4-pyrrolidinedicarboxylate 
• 1140972-11-7 isopropyl (1S,3R,3aS,6aR)-5-methyl-3-phenyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate 
• 1380335-45-4 triisopropyl 5-phenyl-1H-1,2,4-triazole-1,2,3(5H)-tricarboxylate 

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.

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