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Synthesis 2010(18): 3188-3194  
DOI: 10.1055/s-0030-1258183
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Achiral and α-Amino Acid Derived Dicationic Imidazoliophanes

Aleš Mareka, Jiří Kulháneka, W. B. Schweizerb, Filip Bureš*a
a Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 532 10, Czech Republic
Fax: +420(46)6037068; e-Mail: filip.bures@upce.cz;
b Laboratorium für Organische Chemie, ETH-Zürich, Hönggerberg, HCI, Zürich 8093, Switzerland
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Publication History

Received 12 April 2010
Publication Date:
16 July 2010 (online)

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Abstract

Achiral and chiral imidazoliophanes were prepared by N-alkylation of chiral imidazole derivatives featuring an α-amino acid motif and subsequent double quarternization of the imidazole N3-position of the corresponding precyclophanes. Eight new optically pure imidazoliophanes were synthesized in good yields, whereas the molecular structure of one achiral analogue was confirmed by X-ray analysis.

Key words

cyclophanes - imidazoliophanes - amino acids - chiral pool - ligands

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CCDC 757647 contains 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].