Preparative separation of racemic mixtures into the antipodes by complexation gas chromatography on optically active metal coordination compounds

摘要

The present invention describes a method for the preparative separation of racemates (enantiomers, optical isomers, mirror-image isomers). The object is achieved by "complexation gas chromatography". This entails a chiral, non-racemic metal coordination compound being applied, either as solution in an involatile stationary phase (e.g. squalane, silicone oil) or as polymer, to an inactivated support (e.g. Chromosorb, kieselguhr), and packed into a gas chromatography column. Because of the enantiospecific interaction between racemic substrate and chiral stationary phase, preparative separation of racemates is possible in a gas chromatography procedure. The racemates which can be separated in this way comprise chemical compounds which are capable of coordination and which contain, in particular, oxygen, nitrogen and sulphur functionalities. Typical examples are: ketones, ethers, cyclic ethers, acetals, aziridines, thioethers. The method according to the invention is particularly used for racemates which have no suitable functionality for the conventional racemate resolution via diastereomers and which have not to date been amenable to racemate resolution by liquid chromatography. The method is used for racemate resolution of pheromones (e.g. chalcogran, brevicomin), fragrances, flavourings, chiral fine chemicals and chiral radiochemicals. Quantitative preparative separation of all four ... Original abstract incomplete. <IMAGE>