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2000•Collection of Czechoslovak Chemical CommunicationsRequires access

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

Josef Růžička, Ludvı́k Streinz, David Šaman, Zdeněk Havlas, Zdeněk Wimmer, Marie Zarevúcká, Bohumı́r Koutek, L. Lešetický

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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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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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Available 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.

Key concepts: Diastereomer, Chemistry, Derivatization, Steric effects, Chiral derivatizing agent, Resolution (logic), Organic chemistry, Chiral resolution

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