870083-19-5

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 616-34-2 methoxycarbonylmethylamine 
• 5680-79-5 glycine ethyl ester hydrochloride 

Downstream Products

• 1100793-67-6 (2S,3S,4R,5R)-methyl 4-benzoyl-3-phenyl-5-(o-methylphenyl)pyrrolidine-2-carboxylate 
• 1432734-91-2 (2R,3S,4S,5R)-dimethyl-4-benzamido-3-phenyl-5-(2-methylphenyl)pyrrolidine-2,4-dicarboxylate 
• 1350971-24-2 (2R,3R,4S,5R)-methyl 4-nitro-3-(4-nitrophenyl)-5-o-tolylpyrrolidine-2-carboxylate 
• 1130894-66-4 C₂₁H₂₃NO₆S 
• 1130894-39-1 (2R,3R,4S,5R)-dimethyl 4-(phenylsulfonyl)-5-(o-tolyl)pyrrolidine-2,3-dicarboxylate 
• 1040185-10-1 (2R,3S,4S,5S)-methyl 3,4-bis(phenylsulfonyl)-5-o-tolylpyrrolidine-2-carboxylate 

Relevant academic research and scientific papers

Catalytic Aerobic Oxidation and Tandem Enantioselective Cycloaddition in Cascade Multicomponent Synthesis

An efficient multicomponent cascade transformation for the highly diastereo- and enantioselective synthesis of complex natural product inspired polycyclic products from simple starting materials is described. The cascade is initiated by copper-catalyzed a

Switching Diastereoselectivity in Catalytic Enantioselective (3+2) Cycloadditions of Azomethine Ylides Promoted by Metal Salts and Privileged Segphos-Derived Ligands

Catalytic enantioselective 1,3-dipolar cycloaddition between imino esters and electrophilic alkenes, employing chiral metal complexes derived from copper(I) and silver(I) salts and (S)-DM-or (S)-DTBM-Segphos as ligands produces diastereodivergently exo-or

Enantioselective synthesis of 4-aminopyrrolidine-2,4-dicarboxylate derivatives via Ag-catalyzed cycloaddition of azomethine ylides with alkylidene azlactones

A catalytic highly enantioselective silver-DTBM-segphos catalyzed cycloaddition of α-iminoesters with alkylidene azlactones is reported. This procedure provides an effective access to 4-aminopyrrolidine-2,4- dicarboxylate derivatives with high diastereo- and enantioselectivity. The Royal Society of Chemistry 2013.

Silver-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with β-boryl acrylates

The Ag-catalyzed 1,3-dipolar cycloaddition of (?)-β-borylacrylates with azomethine ylides is described. The resulting 3-borylpyrrolidine derivatives were obtained in high yields and complete endo selectivities using AgOAc/ dppe as catalyst system and B(dam) as boryl group. Transformation of the B(dam) group into pinacol borane and oxidation afforded 3-hydroxyproline derivatives in high yields.

The phenylsulfonyl group as a temporal regiochemical controller in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides

(Chemical Equation Presented) Controlling the regioselectivity: The phenylsulfonyl group controlled the regioselectivity in the title reaction to afford pyrrolidine-2,3-dicarboxylates with good regioselectivity and high exo selectivity and enantioselectivity (see scheme). The products are precursors to substituted pyrrolidines and pyrrolines that are not attainable by direct 1,3-dipolar cycloadditions with typical acrylates.

Bis-sulfonyl ethylene as masked acetylene equivalent in catalytic asymmetric [3 + 2] cycloaddition of azomethine ylides

Enantioenriched 3-pyrrolines have been synthesized by highly enantioselective Fesulphos-Cu-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with trans-1,2-bisphenylsulfonyl ethylene, followed by reductive sulfonyl elimination. High levels of reactivity, exoselectivity, and enantioselectivity have been accomplished for a variety of substituted azomethine ylides. This cycloaddition-desulfonylation strategy has been applied as a key step in the enantioselective synthesis of a biologically active C-azanucleoside. Copyright

CuI-Fesulphos complexes: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides

The CuI-Fesulphos catalyst system (≤3 mol %) shows an excellent performance in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. High to very high levels of reactivity, endo/exo selectivity, and enantioselectivity (69->99% ee) are generally achieved with a very wide range of azomethine ylides and dipolarophiles. Based on experimental and computational studies data, a model that accounts for this high enantiocontrol is proposed.

Hydrogen-bonding directed reversal of enantioselectivity

A successful stereochemical reversal was achieved in AgOAc catalyzed [3+2] cycloaddition by the formation of hydrogen bonding between ligand and reactant. This strategy provides an efficient and convenient route to prepare both enantiomers of a chiral compound. DFT studies proposed a reasonable mechanism of the reversal of the enantioselectivity; hydrogen bonding changed the transition state. The strategy may provide some useful hints for ligand design. Copyright

Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones

A general protocol for the enantioselective catalytic 1,3-dipolar cycloaddition of azomethine ylides with aryl vinyl sulfones is described. Nearly complete exo selectivity and enantioselectivities up to 85% ee are attained with Cu(CH3CN)4