339190-42-0

Upstream product

• 100-52-7 benzaldehyde 
• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 66646-88-6 (E)-N-benzylideneglycine methyl ester 
• 100-39-0 benzyl bromide 
• 15028-44-1 DL-phenylalanine methyl ester 

Downstream Products

• 67628-03-9 methyl 2-benzyl-6,8-dioxo-4,7-diphenyl-3,7-diazabicyclo<3.3.0>octane-2-carboxylate 
• 75516-80-2 trimethyl (2R,3R,4S,5R)-2,5-diphenylpyrrolidine-2,3,4-tricarboxylate 
• 75516-80-2 (2S,3R,4S,5R)-2,5-Diphenyl-pyrrolidine-2,3,4-tricarboxylic acid trimethyl ester 
• 75516-82-4 (2S,3R,4S,5R)-2-Benzyl-5-phenyl-pyrrolidine-2,3,4-tricarboxylic acid trimethyl ester 
• 75516-82-4 (2S,3S,4R,5R)-2-Benzyl-5-phenyl-pyrrolidine-2,3,4-tricarboxylic acid trimethyl ester 
• 75516-82-4 trimethyl 2-benzyl-c-5-phenylpyrrolodine-r-2,c-3,c-4-tricarboxylate 
• 75516-82-4 trimethyl 2-benzyl-c-5-phenylpyrrolodine-r-2,t-3,t-4-tricarboxylate 
• 86748-68-7 Methyl 2-Benzyl-2-(benzylidenamino)-4-pentynoate 
• 75516-80-2 (2R,3R,4R,5R)-2,5-Diphenyl-pyrrolidine-2,3,4-tricarboxylic acid trimethyl ester 
• 75516-80-2 (2S,3S,4S,5R)-2,5-Diphenyl-pyrrolidine-2,3,4-tricarboxylic acid trimethyl ester 
• 75516-82-4 (2S,3R,4R,5R)-2-Benzyl-5-phenyl-pyrrolidine-2,3,4-tricarboxylic acid trimethyl ester 
• 75516-82-4 (2S,3S,4S,5R)-2-Benzyl-5-phenyl-pyrrolidine-2,3,4-tricarboxylic acid trimethyl ester 
• 188760-07-8 methyl [(2R,4S,5S,S_S)-4-benzyl-2,5-diphenyl-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate 

Relevant academic research and scientific papers

1,3-Dipolar cycloadditions of acetylenic sulfones in solution and on solid supports

(Chemical Equation Presented) Several representative acetylenic sulfones were immobilized on a polymer support derived from Merrifield resin by means of ester linkers that were used to couple free carboxylic acid groups on the solid support with benzylic hydroxyl functions on the arylsulfonyl moieties of the acetylenes. Several examples of reversed ester linkers, using Merrifield resin directly, were also successfully prepared. The 1,3-dipolar cycloadditions of the solid-supported acetylenic sulfones were investigated with a series of 1,3-dipoles, including benzyl azide, ethyl diazoacetate, diazomethane, as well as representative nitrile oxides, nitrile imines, nitrile ylides, nitrones, azomethine imines, azomethine ylides, munchnones, and sydnones. In general, analogous cycloadditions were also performed with acetylenic sulfones in solution phase for comparison. The cycloadditions typically afforded good to excellent yields of the desired products in both solution and solid phase, although the latter reactions sometimes required more vigorous conditions. Except in the case of benzyl azide and diazo compounds, where mixtures of regioisomers were obtained, the other 1,3-dipoles reacted with high regioselectivity and afforded essentially unique regioisomers. Cleavage of the products from the resin was smoothly effected by alkaline hydrolysis, while several attempts at reductive desulfonylation with sodium amalgam or samarium diiodide-HMPA resulted in N-O or C-O scission, in addition to cleavage from the polymer. The method provides access to a number of important classes of heterocycles, including variously substituted and functionalized triazoles, pyrazoles, 1,2-oxazoles, pyrroles, as well as their dihydro and bicyclic analogues. The success of the cycloadditions on polymer supports paves the way to future investigations of sequential transformations leading to libraries of useful heterocycles.

Novel highly functionalized benzoylaminocarbothioyl pyrrolidine from benzoylisothiocyanate and substitueted pyrrolidine derived from α-aminoasit ester via imine -azomethine ylide-1,3-dipolar cycloaddition cascade

A series of novel highly functionalized benzoylaminocarbothioyl pyrrolidines were prepared by the reaction of benzoylisothiocyanate with substitueted pyrrolidine derived from α -aminoasit ester via metal catalsed imine -azomethine ylides-1,3-Dipolar Cycloaddition in excellent yield. An example of chiral version benzoylaminocarbothioyl pyrrolidine were also reported. The chirality oryginated from menthyl acrylate as chiral dipolarophile in the cycloaddition cascade and induced three novell chiral centres.

The synthesis of β-strand mimetic templates via regioselective 1,3-dipolar cycloaddition with vinylsulfone

We have developed a practical synthetic route to constrained β-strand mimetic templates by regioselective 1,3-dipolar cycloaddition of azomethine imines with vinyl sulfone. A small library of β-strand mimetic templates was generated which include potent and selective inhibitors of serine proteases.