Enantioselective anion exchangers based on cinchona alkaloid-derived carbamates: Influence of C8/C9 stereochemistry on chiral recognition

Chirality

Volumn 11, Issue 7, 1999, Pages 522-528

  Maier, Norbert M ^a   Nicoletti, Lorenzo ^a   Lämmerhofer, Micheal ^a   Lindner, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Carbamates; Chiral recognition mechanism; Chiral selector; Cinchona alkaloids; Enantioselective anion exchangers; N protected amino acids; Selector selectand complex; X ray structure

Indexed keywords

CARBAMIC ACID DERIVATIVE; CINCHONA ALKALOID; QUINIDINE; QUININE;

ANION EXCHANGE; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

ANTIMALARIALS; CARBAMATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CINCHONA ALKALOIDS; CRYSTALLOGRAPHY, X-RAY; MODELS, CHEMICAL; MOLECULAR CONFORMATION; QUINIDINE; QUININE; STEREOISOMERISM;

EID: 0032808073     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:7<522::AID-CHIR2>3.0.CO;2-U     Document Type: Article

References (8)

1. Lämmerhofer M, Lindner W. Quinine and quinidine derivatives as chiral selectors I. Brush type chiral stationary phases for high-performance liquid chromatography based on cinchonan carbamates and their application as chiral anion exchangers. J Chromatogr A 1996; 741:33-48.
2. Kleidernigg OP, Lämmerhofer M, Lindner W. Determination of enantiomeric purity of D- and L-proline using a new indirect and direct chiral separation technique by HPLC; method development and evaluation of accuracy. Enantiomer 1996;1:387-402.
3. Lämmerhofer M, Di Eugenio PE, Molnar I, Lindner W. Computerized optimization of the HPLC enantioseparation of a mixture of DNP-amino acids on a quinidine carbamate type chiral stationary phase using Drylab. J Chromatgr B 1997;689:123-135.
4. Piette V, Lämmerhofer M, Bischoff K, Lindner W. HPLC enantioseparation of N-protected amino acids using non-porous silica modified by a quinine carbamate as chiral stationary phase. Chirality 1997;9:157-161.
5. Lindner W, Lämmerhofer M, Maier NM. Cinchonan based chiral selectors for separation of stereoisomers. PCT/EP 97/02888.
6. Dijkstra GDH, Kellogg RM, Wynberg H, Svendsen JS, Marko I, Sharpless KB. Conformational study of cinchona alkaloids. A combined NMR, molecular mechanics and X-ray approach. J Am Chem Soc 1989;111:8069-8076.
7. Hiratake J, Inagaki M, Yamamoto Y, Oda J. Enantiotopic-group differentiation. Catalytic asymmetric ring-opening of prochiral cyclic acid anhydrides with methanol, using cinchona alkaloids. J Chem Soc Perkin Trans I 1987;1058.
8. Veigl E, Böhs B, Mandl A, Krametter D, Lindner W. Comparison of (S)-N-(3,5-dinitrobenzoyl)tyrosine derivatives as chiral selectors for high performance liquid chromatographic enantioseparations. J Chromatogr A 1995;694:135-150.