134356-90-4

Upstream product

• 868-72-4 dimethyl rac-2,5-dibromohexanedioate 
• 100-46-9 benzylamine 
• 868-72-4 dimethyl (2R,5S)-2,5-dibromohexanedioate 
• 111-50-2 Adipic acid dichloride 
• 868-72-4 dimethyl 2,5-dibromohexanedioate 
• 29548-86-5 2,5-dibromohexanedioyl dichloride 
• 124-04-9 Adipic acid 
• 102508-03-2 cis-2,5-dimethyl N-benzylpyrrolidine-2,5-dicarboxylate 
• 51483-87-5 1-Benzyl-2,5-pyrrolidindicarbonsaeure-dimethylester 

Downstream Products

• 111138-50-2 (2S,5S)-1-Benzyl-pyrrolidine-2,5-dicarboxylic acid monomethyl ester 
• 281668-36-8 meso-1-benzyl-2,5-bis(methoxycarbonyl)-2,5-dimethylpyrrolidine 

Relevant academic research and scientific papers

Synthesis of both enantiomers of C2 symmetric trans-2,5- bis(hydroxymethyl)pyrrolidine. Lipase mediated sequential kinetic resolutions

Lipase mediated sequential kinetic resolution has been employed to give both enantiomers of trans-2,5-bis(hydroxymethyl)pyrrolidine in optically pure form. The effect of different parameters on the ee and yields in these resolutions are also reported.

A mechanochemical approach to access the proline-proline diketopiperazine framework

Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline-proline dipeptides under solvent-free conditions. A deprotection-cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro-Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.

Switching and Conformational Fixation of Amides Through Proximate Positive Charges

Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization. Taking charge of conformation: Tertiary amides, which usually occur as cis/trans mixtures, can be effectively shifted to the cis conformation by placing a positive charge in close proximity to the amide carbonyl. This effect was used to prepare cis-configured prolyl amides and to facilitate a strongly rotamer-dependent radical cyclization.

Amino Acids, 14. - Diastereoselective Addition of Benzenesulfenyl Chloride to 1-Acryloylproline Esters

(S)-Proline esters (S)-1 react with acryloyl chloride (2) to give 1-acryloylproline esters (S)-3 in good yields.Addition of benzenesulfenyl chloride (6) to (S)-3 at -95 deg C in dichloromethane results in 1-proline esters

Base-Catalysed Epimerization Behavior and Unusual Reactivity of N-Substituted Derivatives of 2,5-Dicarbalkoxypyrrolidine. Preparation of a Novel Mixed Carbamic Carbonic Anhydride by a 4-(Dimethylamino)pyridine-Catalyzed Acylation

The equilibration of cis-trans isomers of 1-substituted 2,5-dicarbalkoxypyrrolidine derivatives (1 = CH2Ph, H, CN, CO2R) results in nearly 1:1 mixtures, contrary to a literature report for 1-benzyl-2,5-dicarbalkoxypyrrolidine.Apparent conversion to the tr