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Solid state isomerisation of atropodiastereomers : A promising method to obtain high diastereomeric ratios.
Published: 11 September 2000 by MDPI in The 4th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Abstract: A series of imides with two chirality axes have been synthesized. Comparatively low activation barriers to isomerisation and, at the same time, high melting points lead to interesting behaviors of these compounds: whereas thermodynamic equilibria of nearly 50:50 diastereomeric ratios were reached rapidly in solution at 110°C, ratios up to 99:1 in favor of one diastereomer have been observed after prolonged heating above the same temperature of the mixture of diastereomers in the solid state. Crystallographic and differential scanning calorimetric (DSC) techniques have been used to support these studies and their interpretation.