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Cyclodextrin Derivatives as Chiral Selectors—Investigation of the Interaction with ( R,S )‐Methyl‐2‐chloropropionate by Enantioselective Gas Chromatography, NMR Spectroscopy, and Molecular Dynamics Simulation
Author(s) -
Köhler Jutta E. H.,
Hohla Manfred,
Richters Martina,
König Wilfried A.
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199203191
Subject(s) - enantiomer , chemistry , enantioselective synthesis , cyclodextrin , molecular dynamics , nuclear magnetic resonance spectroscopy , gas chromatography , chiral derivatizing agent , chiral column chromatography , reagent , organic chemistry , stereochemistry , computational chemistry , chromatography , catalysis
The greater stability of the complex of methyl ( S )‐2‐chloropropionate (( S )‐ 1 ) and the hydrophobic cyclodextrin derivative 2 , is deduced from its characterization by gas chromatography and NMR spectroscopy as well as from molecular dynamics simulations of the ( R,S )‐ 1/2 , ( R )‐ 1/2 , and ( S )‐ 1/2 systems: on complexation the 1 H NMR signals of the ( S ) enantiomer undergo a downfield shift of up to Δδ = 0.5 relative to those of the ( R ) enantiomer. Thus, cyclodextrins can be used not only for enantiomeric separations, but also as chiral shift reagents. R 2 = R 6 = n ‐pentyl, R 3 = acetyl.