Facile Synthesis of Enantiomerically Pure Architectures Based on Triphenylene Ketals

Martin Bomkamp; Aleksander Artiukhov; Olga Kataeva; Siegfried R. Waldvogel

doi:10.1055/s-2007-965986

FEATUREARTICLE

Facile Synthesis of Enantiomerically Pure Architectures Based on Triphenylene Ketals

Martin Bomkamp^a, Aleksander Artiukhov^a, Olga Kataeva^a,b, Siegfried R. Waldvogel*^a
^a Rheinische Friedrich-Wilhelms-Universität Bonn, Kekulé-Institut für Organische Chemie und Biochemie, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
^b A. E. Arbuzov Institute of the Russian Academy of Sciences, Arbuzov Street 8, Kazan 420088, Russian Federation
Fax: +49(228)739608; e-Mail: waldvogel@uni-bonn.de;

Abstract

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Abstract

Employing naturally derived (-)-isosteviol for the construction of chirally modified triphenylene ketals resulted in very rigid supramolecular clefts that exhibit a mutual distance of about 20 Å between the functional groups. Since the stereodirecting groups of these novel architectures are located in the backbone, an open receptor geometry is established.

Key words

receptor - supramolecular chemistry - terpenoids - chirality - triphenylene ketal

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Referenzen

References

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Programs used, data collection:

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Structure solution SIR97:

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Implemented in the WINGX package:

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Structure refinement by full-matrix least-squares against F² using SHELXL-97:

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The absolute configuration was assessed by Flack’s enantiopole parameter 0.02(6).

CCDC 630916 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk].