Collect. Czech. Chem. Commun. 2000, 65, 695-707

Chlorofluoroacetic Acid as a Highly Versatile Derivatizing Agent: Assignment of Stereochemistry to Esters of Chiral Alcohols

Josef Růžičkaa, Ludvík Streinzb,*, David Šamanb, Zdeněk Havlasb, Zdeněk Wimmerb, Marie Zarevúckab, Bohumír Koutekb and Ladislav Lešetickýa

a Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
b Institute of Organic Chemistry and Biochemistry, 166 10 Prague 6, Czech Republic


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.

Keywords: Chiral derivatizing agents; Enantiomers; Resolution; Absolute configuration; Secondary alcohols; Correlations; HPLC; NMR spectroscopy.

References: 68 live references.