- Synthesis, Absolute Configuration, and Circular Dichroism of the Enantiomers of Fluorosuccinic Acid
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Diethylaminosulphur trifluoride (DAST) converts (2S)- and (2R)-malate esters into the enantiomeric fluorosuccinate esters. (2S,3R)-Malate, obtained from fumarate by fumarase-catalysed hydration in deuterium oxide, was used to show that the reaction with DAST occurs stereospecifically with inversion of configuration.Conversion of (2S)-aspartic acid into fluorosuccinate with sodium nitrite in polyhydrogen fluoride-pyridine occurs predominantly with retention of configuration.The circular dichroic spectra of (2S)- and (2R)-fluorosuccinic acids and their methyl esters are 'anomalous' and consequently the absolute configuration previously assigned to a Pseudomonal metabolite, (+)-fluorosuccinic acid, is shown to be erroneous.
- Lowe, Gordon,Potter, Barry V. L.
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p. 2029 - 2032
(2007/10/02)
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