86091-69-2Relevant academic research and scientific papers
Biphasic enantioselective partitioning studies using small-molecule chiral selectors
Snyder, Seth E.,Carey, James R.,Pirkle, William H.
, p. 7562 - 7567 (2007/10/03)
Enantioselective partitioning of racemic N-3,5-(dinitrobenzoyl)leucine or racemic naproxen was studied using a two-component chiral phase transfer approach. A combination of an achiral ion-pairing reagent and a chiral complexing agent (selector) is necessary to effect enantioselective partitioning between an aqueous bicarbonate solution and a nonpolar organic solvent. In these biphasic resolutions, the interplay between the ion-pairing reagent and the selector is essential for maximizing enantioselectivities. Furthermore, the lipophilicity of the ion-pairing reagent, the concentration of the ion-pairing reagent and selector, and the polarity of the organic solvent all exert a considerable influence on the biphasic process. In this manuscript, we conduct optimization studies through analysis of solvent, concentration and ion-pairing effects. Conclusions concerning the mechanistic rationale behind enantioselective partitioning are given.
Enantioselective hydrolysis of N-acylated α-amino esters at a biphasic interface: Tandem reaction kinetic resolution using a chiral complexing agent
Snyder, Seth E.,Pirkle, William H.
, p. 3283 - 3286 (2007/10/03)
equation presented Highly enantioselective hydrolytic kinetic resolutions of esters derived from N-acylated α-amino acids proceed rapidly at hydrocarbon/water interfaces in the presence of a proline-derived chiral selector. When performed in tandem with an enantioselective biphasic esterification reaction, esters of 100% enantiomeric excess are obtained.
3,5-DINITROBENZOYL AMINO ACID ESTERS. BROADLY APPLICABLE CHIRAL SOLVATING AGENTS FOR NMR DETERMINATION OF ENANTIOMERIC PURITY.
Pirkle, William H.,Tsipouras, Athanasios
, p. 2989 - 2992 (2007/10/02)
Methyl esters of N-(3,5-dinitrobenzoyl)-amino acids have been used as chiral solvating agents to induce NMR spectral nonequivalence between the enantiomers of a broad array of solutes.
