153242-44-5

Upstream product

• 909405-19-2 (2S,5RS)-methyl 1-methoxycarbonyl-5-phenyl-pyrrolidine-2-carboxylate 
• 4931-66-2 methyl (S)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 
• 1611470-49-5 (S)-methyl 2-((tert-butoxycarbonyl)amino)-5-oxo-5-phenylpentanoate 
• 501096-26-0 (2RS,5S)-1-(tert-butoxycarbonyl)-2-phenyl-5-carbomethoxy-3-pyrroline 
• 734533-49-4 (S)-methyl 2-(ethoxycarbonyl)amino-5-oxo-5-phenylpentanoate 
• 78342-49-1 (S)-2-Amino-5-phenyl-pent-4-ynoic acid methyl ester 
• 591-50-4 iodobenzene 
• 848132-12-7 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-phenyl-4-pentynoate 
• 848132-13-8 methyl (2S)-5-phenyl-3,4-dihydro-2H-2-pyrrolecarboxylate 
• 434326-89-3 methyl (6R,8R)-(-)-8-phenyl-1,4-dithia-7-aza-spiro[4.4]nonane-6-carboxylate 
• 211614-52-7 (2S,5R)-5-Phenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 434326-81-5 methyl (S_S,R)-(+)-2-diazo-3-oxo-5-(p-toluenesulfinylamino)-5-phenylpentanoate 

Downstream Products

• 1601475-96-0 (2S,5R)-1-benzyl-2-hydroxymethyl-5-phenylpyrrolidine 
• 153242-42-3 (2S,5R)-1-<2-(tert-butoxycarbonylamino)-1-oxo-ethyl>-5-phenyl-pyrrolidine-2-carboxylic acid 
• 153242-41-2 tert-butyl (2S,5R)-1-(2-aminoacetyl)-5-phenylprolinate 
• 177741-93-4 (2S,5R)-1-[2-((S)-2-Acetylsulfanyl-3-phenyl-propionylamino)-acetyl]-5-phenyl-pyrrolidine-2-carboxylic acid methyl ester 
• 177930-60-8 (2S,5R)-1-[2-((R)-2-Acetylsulfanyl-3-phenyl-propionylamino)-acetyl]-5-phenyl-pyrrolidine-2-carboxylic acid methyl ester 
• 177741-97-8 (2S,5R)-1-{2-[(S)-2-Acetylsulfanyl-3-(4-benzyloxycarbonyloxy-phenyl)-propionylamino]-acetyl}-5-phenyl-pyrrolidine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of cis-2,5-disubstituted pyrrolidines via diastereoselective reduction of N-acyl iminium ions

A new procedure for forming cis-2,5-disubstituted pyrrolidines having unsaturated side chains has been developed that features the diastereoselective reduction of N-acyl iminium ions, which were formed in situ by acid-catalyzed cyclizations of unsaturated

Enantioselective CpxRhIII-Catalyzed Carboaminations of Acrylates

Enantioselective carboaminations of olefins constitute an attractive strategy for a rapid increase in molecular complexity from readily available starting materials. Reported here is an intermolecular asymmetric carboamination of acrylates using rhodium(III)-catalyzed alkenyl C?H activations of N-enoxysuccinimides to generate the nitrogen and carbon portion for the transfer. A rhodium complex equipped with a tailored bulky trisubstituted chiral Cpx ligand ensures carboamination chemoselectivity as well high levels of enantioinduction. The transformation operates under mild reaction conditions at ambient temperatures and provides access to a variety of α-amino esters in good yields and excellent enantiomeric ratios of >99.5:0.5.

Synthesis of Bicyclic and Tricyclic Chiral Guanidinium Salts by an Intramolecular Alkylation Approach

Synthetic studies leading to three new types of chiral guanidinium scaffolds are described. Structures of interest include bicyclic guanidine derivatives with various substitution patterns around the guanidine core, as well as a highly rigid tricyclic scaffold. The challenging targets were accessed by application of mercury(II)-promoted guanylation of N-Boc-substituted thioureas and Ishikawa's desulfurative cyclization. In addition to our synthetic logics, a scalable synthesis of the tricyclic guanidinium salt is presented.

Flexible and modular syntheses of enantiopure 5-cis-substituted prolinamines from l-pyroglutamic acid

A wide range (25 examples) of 5-cis-substituted prolinamines is prepared in five to ten steps starting from cheap l-pyroglutamic acid. Three routes, differing mainly in the order of introduction of the substituents at the 5-cis position, the pyrrolidine nitrogen atom, and the exocyclic amino function, are successfully developed.

Binap-silver salts as chiral catalysts for the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes

Binap-AgSbF6 catalyzed 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes are described and compared with analogous transformations mediated by other Binap-silver(I) salt complexes. Maleimides and 1,2-bis(phenylsulfo

PYRROLIDINE OR THIAZOLIDINE CARBOXYLIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERSAS AS AGONISTS OF G- PROTEIN COUPLED RECEPTOR 43 (GPR43)

The present invention is directed to novel compounds of formula (I) and their use in treating and/or preventing metabolic diseases.

A new sparteine surrogate for asymmetric deprotonation of N-Boc pyrrolidine

(Chemical Equation Presented) The s-BuLi complex of a cyclohexane-derived diamine is as efficient as s-BuLi/(-)-sparteine for the asymmetric deprotonation of N-Boc pyrrolidine. This is the first example of high enantioselectivity using a non-sparteine-like diamine in such reactions. The ( S, S)-diamine is a useful (+)-sparteine surrogate and was utilized in short syntheses of (-)-indolizidine 167B and an intermediate for the synthesis of the CCK antagonist (+)-RP 66803.

Novel approach to 5-substituted proline derivatives using a silver-catalyzed cyclization as the key step

(Chemical Equation Presented) A novel synthetic approach to the synthesis of enantiomerically pure 2,5-disubstituted pyrrolines is described. The methodology involves a Ag-catalyzed 5-endo-dig cyclization of enantiopure aryl-substituted acetylene-containi

Probing the stereoselectivity of the Heck arylation of endocyclic enecarbamates with diazonium salts. Concise syntheses of (2S,5R)-phenylproline methyl ester and Schramm's C-azanucleoside.

[reaction: see text] The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coor

Asymmetric synthesis of substituted prolines from delta-amino beta-ketoesters. Methyl (2S,5R)-(+)-5-phenylpyrrolidine-2-carboxylate.

[reaction: see text]. Metal carbenoid chemistry is used to convert delta-amino beta-ketoesters into 5-substituted 3-oxo prolines, which expands the utility of this class of polyfunctionalized chiral building blocks.