Synthesis, absolute configuration, and circular dichroism of the enantiomers of fluorosuccinic acid
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 2029-2032
- https://doi.org/10.1039/p19800002029
Abstract
Diethylaminosulphur trifluoride (DAST) converts (2S)- and (2R)-malate esters into the enantiomeric fluorosuccinate esters. (2S,3R)-[3-2H1]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.This publication has 1 reference indexed in Scilit:
- Convenient general preparation of oxygenated monofluoro- and gem-difluoro-5a-androstanes using diethylaminosulphur trifluorideJournal of the Chemical Society, Chemical Communications, 1978