57043-01-3

Upstream product

• 1560-11-8 cyclopent-1-enecarboxylic acid 
• 136315-71-4 (±)-trans-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid 
• 22031-52-3 cis-2-aza-3-oxobicyclo<3.2.0>heptane 

Downstream Products

• 61935-49-7 trans-2-carbobenzyloxyamino-1-cyclopentanecarboxylic acid 
• 119993-56-5 ethyl trans-2-amino-1-cyclopentanecarboxylate hydrochloride 
• 135053-11-1 trans-2-aminocyclopentanecarboxamide 
• 114745-58-3 {2-[((1S,2S)-2-Benzyloxycarbonylamino-cyclopentanecarbonyl)-amino]-acetylamino}-acetic acid ethyl ester 
• 136237-68-8 N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-trans-2-aminocyclopentanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition-cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic β-amino acids

A combination of sulfanyl radical addition-cyclization of the oxime ethers and hydrazones connected with alkenes and subsequent conversion of a phenylsulfanylmethyl group to a carboxyl group provides a novel method for the construction of the cyclic β-amino acids. Upon treatment with thiophenol in the presence of AIBN, the oxime ethers and hydrazones smoothly underwent sulfanyl radical addition-cyclization to give the 2-(phenylsulfanylmethyl)cycloalkylamine. This method was successfully applied to the practical synthesis of 2-aminocyclopentanecarboxylic acid and 4-amino-3-pyrrolidinecarboxylic acid.

High-Performance Liquid Chromatographic Enantioseparation of Cyclic β-Amino Acids on Zwitterionic Chiral Stationary Phases Based on Cinchona Alkaloids

Stereoselective high-performance liquid chromatographic separations of eight sterically constrained cyclic β-amino acid enantiomer pairs were carried out using the newly developed Cinchona alkaloid-based zwitterionic chiral stationary phases Chiralpak ZWIX(+) and ZWIX(-). The effects of the mobile phase composition, the nature and concentrations of the acid and base additives, the counterions and temperature on the separations were investigated. The changes in standard enthalpy, Δ(ΔH°), entropy, Δ(ΔS°), and free energy, Δ(ΔG°), were calculated from the linear van't Hoff plots derived from the ln α vs. 1/T curves in the studied temperature range (10-50°C). The values of the thermodynamic parameters depended on the nature of the selectors and the structures of the analytes. Unusual temperature behavior was observed on the ZWIX(-) column: decreased retention times were accompanied by increased separation factors with increasing temperature. On the ZWIX(+) column only enthalpically, whereas on the ZWIX(-) column both enthalpically and entropically driven separations were observed. The elution sequence was determined in all cases and was observed to be the opposite on ZWIX(+) and on ZWIX(-). Chirality 27:563-570, 2015.

Synthesis of novel sila-substituted β-amino acids

A highly efficient and stereoselective synthesis of unnatural cyclic sila-substituted β-amino acids has been developed from simple starting materials. The key step is nucleophilic ring opening of an intermediate aziridine with an umpolung synthon for the

A novel preparation of 2-aminocyclopentanecarboxamides

Different syntheses of cis- and trans-2-aminocyclopentanecarboxamides were studied. A convenient and effective method was devised for the preparation of cis-2-aminocyclopentanecarboxamide derivatives starting from the readily available 6-tert-butoxycarbon

An improved synthesis of enantiopure β-amino acids

An improved method for the preparation of both the enantiopure β-amino acids is presented. The diastereomer benzyl β-amino esters, obtained by stereoselective reduction of β-enamino esters, were separated and hydrogenolyzed to the free enantiopure β-amino acids.