Abstract
Stereochemistry of a series of diastereomeric esters obtained from chiral alcohols 1a-21a by derivatization with (S)- or (R)-chlorofluoroacetic acid was correlated with their LC and GC separation (∆tr) and NMR resolution (∆δ). Both the chromatographic and NMR spectral behavior of respective diastereomers was found to follow systematic rules reflecting their steric arrangement. Moreover, identical conformations of the esters seem to be preferred in solution as well as in the chromatographic processes. Reasons underlying this behavior are discussed.
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