7495-01-4Relevant articles and documents
Biphasic enantioselective partitioning studies using small-molecule chiral selectors
Snyder, Seth E.,Carey, James R.,Pirkle, William H.
, p. 7562 - 7567 (2005)
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.
Two-component chiral phase transfer catalysts: enantioselective esterification of an N-acylated amino acid.
Pirkle,Snyder
, p. 1821 - 1823 (2001)
[see reaction]. The first example of a two-component chiral phase transfer catalyst is described which, operating in a biphasic solvent system, preferentially esterifies one enantiomer of a racemic N-acylated amino acid. The two-component catalyst is comprised of an achiral quaternary ammonium ion and a proline-derived chiral selector initially developed for the liquid chromatographic separation of enantiomers.
Theoretical and Experimental Studies of Chiral Recognition in Charged Pirkle Phases
Lee, One-Sun,Jang, Yun Hee,Cho, Young Gi,Hyun, Myung Ho,Kim, Hie-Joon,Chung, Doo Soo
, p. 232 - 233 (2001)
The role of electrostatic interactions in enantioselective separation was demonstrated. Enantioselective separation of N-(3,5-dinitrobenzoyl)leucine and its esterified analogue was investigated by (S)-phenylglycine-based HPLC under an intermediate pH, and examined with a relaxed scan calculation combined with a Monte Carlo conformation search.
COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS
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Page/Page column 45-49; 51, (2010/12/31)
The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.