Studies on inclusion resolution : gaining insight into chemical and physical properties
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[S.l. : s.n.]
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Inclusion is a process where two or more compounds crystallise together in a mixed, but regular, crystal lattice. Inclusion resolution is a relatively new way for separating enantiomers from a racemic mixture which employs inclusion with enantiopure compounds as hosts. An enantiopure host compound can lead to chiral recognition, and thus to selective inclusion, of one of the enantiomers of a racemic guest. Thus, it can be used for the resolution of this guest compound in a process which is similar to classical resolution using diastereomeric salts. Inclusion resolution, however, has a number of potential advantages when compared to classical resolution, such as the capability to resolve uncharged compounds and a better potential for the application of asymmetric transformation. The first successful examples of efficient inclusion resolutions, mostly using Taddols as host compounds (diaryl carbinol derivatives of tartaric acid), were described by Toda in the end 80's. Only a limited number of other hosts, such as dipeptides or lactic acid derivatives, have since then been developed and applied in inclusion resolution. In contrast to classical resolution very little is known about the physico-chemical background, thermodynamics and other fundamental aspects of inclusion resolution. A large part of the study described in this thesis was therefore aimed at elucidating some fundamental aspects of inclusion resolution, especially from a point of view of industrial applicability. Several Taddols and some phenylglycine dipeptides were chosen for a thorough study of fundamental aspects, scope and limitations of inclusion resolution
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