NMR spectroscopic investigations involving extensive use of ROESY and DOSY techniques and comparison with silylated-acetylated linear dextrins as acyclic model compounds shed light on the origin of the phenomenon of enantiodiscrimination of fluorinated α-amino acid derivatives by heptakis[2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)]-β- cyclodextrin. The effectiveness and versatility of the cyclic derivatized oligosaccharide as a chiral solvating agent for the NMR determination of enantiomeric purity in the same class of compounds is demonstrated. A regular correlation between the relative positions of enantiomers’ signals and absolute configurations is observed.

External vs. internal interactions in the enantiodiscrimination of fluorinated alpha-amino acid derivatives by heptakis[(2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)]-beta-cyclodextrin, a powerful chiral solvating agent for NMR spectroscopy

UCCELLO BARRETTA, GLORIA;BALZANO, FEDERICA;
2008

Abstract

NMR spectroscopic investigations involving extensive use of ROESY and DOSY techniques and comparison with silylated-acetylated linear dextrins as acyclic model compounds shed light on the origin of the phenomenon of enantiodiscrimination of fluorinated α-amino acid derivatives by heptakis[2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)]-β- cyclodextrin. The effectiveness and versatility of the cyclic derivatized oligosaccharide as a chiral solvating agent for the NMR determination of enantiomeric purity in the same class of compounds is demonstrated. A regular correlation between the relative positions of enantiomers’ signals and absolute configurations is observed.
UCCELLO BARRETTA, Gloria; Balzano, Federica; Pertici, F.; Jicsinszky, L.; Sicoli, G.; Schurig, V.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/122731
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