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External vs. Internal Interactions in the Enantiodiscrimination of Fluorinated α‐Amino Acid Derivatives by Heptakis[2,3‐di‐ O ‐acetyl‐6‐ O ‐( tert ‐butyldimethylsilyl)]‐β‐cyclodextrin, a Powerful Chiral Solvating Agent for NMR Spectroscopy
Author(s) -
UccelloBarretta Gloria,
Balzano Federica,
Pertici Francesca,
Jicsinszky Laszlo,
Sicoli Giuseppe,
Schurig Volker
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701113
Subject(s) - chemistry , enantiomer , acetylation , cyclodextrin , amino acid , oligosaccharide , stereochemistry , organic chemistry , biochemistry , gene
NMR spectroscopic investigations involving extensive use of ROESY and DOSY techniques and comparison withsilylated‐acetylated linear dextrins as acyclic model compounds shed light on the origin of the phenomenon ofenantiodiscrimination 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)