Abstract
The thesis is about the resolution of racemates, which is still the most convenient and commonly applied method to obtain optically pure products, both in the fine-chemical industry and in the laboratory. From an industrial point of view classical resolution using diastereomeric salts still represents a viable technique because of its simplicity and robustness. A relatively new and unexplored concept is the racemate resolutions of uncharged molecules by using neutral host-guest inclusion complexes, the inclusion resolution. This technique is based on chiral discrimination and recognition in the crystal lattice of the inclusion compound. This lattice, being held together by hydrogen bonds and weak van der Waals interactions, is much weaker than in comparable diastereomeric salts. An important lead was provided by the work of Toda et al. on the Taddols and by Weber et al. on diphenylcarbinol derivatives of lactic acid. Inspired by the interesting results reported by these and other authors, inclusion resolution was studied with the aim of expanding the scope and determining the limitations of this method, especially in view of possible industrial applicability. The invention of Dutch Resolution (DR), which is a new approach to classical resolution via diastereomeric salts with a higher success rate, constitutes a new tool. DR applies mixtures of structurally closely related resolving agents instead of a single agent. The availability of a wide range of structurally similar inclusion host molecules offered the opportunity to test Dutch Resolution in inclusion resolution. It is also described the efforts to examine and explore the family concept using a matrix of twelve amino acid derivatives. These compounds are derived from the amino acids Lalanine, L-phenylglycine and L-phenylalanine and can be readily prepared on mole scale. Obviously, these 12 compounds bear strong structural similarities, are stereochemically homogenous and should, thus, represent families of molecules
