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Success Rate in a Chiral Separation: Towards a Better Separation Machinery

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Molecular Recognition and Inclusion

Abstract

Optical resolution is a very fundamental object in chemistry. Although there are different techniques for the enantiomer separation of acids and bases the methods for optical resolution of non-acidic and non-basic compounds in a preparative scale are only rare. Making use of the crystalline inclusion phenomena is a promising new approach to fill this gap[l]. Host compounds having this particular feature of crystalline inclusion formation may be designed according to some basic principles such a rigid framework, attached functional groups and bulky substituents that make a host compund hard to crystallize without a proper spatial/functional complement thus forming a clathrate (Fig. 1) [2]. The clever installment of chirality gives rise to high enantioselectivity at clathrate formation. Ready availability of these blocks in optically resolved form arising from a natural chiral source makes them attractive [3].

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References

  1. E. Weber, (1995), in ‘Kirk-Othmer Encyclopedia of Chemical Technology’, 4th ed., Vol. 14 (Ed.: J.I. Kroschwitz), Wiley, New York, pp. 122–154.

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  2. E. Weber, (1996), in ‘Comprehensive Supramolecular Chemistry’, 4th ed., Vol. 6 (Solid State Supramolecular Chemistry: Crystal Engineering), Eds.: R. Bishop, D.D. MacNicol, F. Toda, Elsevier Science, Oxford, Ch. 18, pp. 535–592.

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  3. E. Weber and C. Wimmer, (1993), Optical resolution by Crystalline Inclusion Formation Using New Lactic Acid Derived Hosts, Chirality, 5, 315–319.

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  4. P.P. Korkas, E. Weber, M. Czugler, G. Naray-Szabó, New Terpenoid Hosts for Chrial Recognition: Crystal Structure and Molecular Modelling Study of an Inclusion Complex with (S)-(+)-Phenyloxirane, J. Chem. Soc. Chem. Commun., 1995, 2229–2230.

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  5. M. Czugler, P. P. Korkas, P. Bombicz, W. Seichter, E. Weber, (1996), Chiral Separation Machinery Using New Crystalline Inclusion Hosts. Match / Mismatch in the Enantiomer Recognition of (R,S)-l-Methoxy-2-propanol Effected by a Borneol / Fenchol Building Block Exchange in the Host Molecule Chirality, 8, in the press.

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© 1998 Springer Science+Business Media Dordrecht

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Czugler, M., Weber, E., Korkas, P.P. (1998). Success Rate in a Chiral Separation: Towards a Better Separation Machinery. In: Coleman, A.W. (eds) Molecular Recognition and Inclusion. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-5288-4_45

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  • DOI: https://doi.org/10.1007/978-94-011-5288-4_45

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-6226-8

  • Online ISBN: 978-94-011-5288-4

  • eBook Packages: Springer Book Archive

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