PDF herunterladen
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
Weitere Informationen

Publikationsverlauf

Received 12 April 2010
Publikationsdatum:
16. Juli 2010 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

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

    References

  • 1 Gibson SE. Lecci C. Angew. Chem. Int. Ed.  2006,  45:  1364 
    CrossrefSuche in Google Scholar
  • 2 Katritzky AR. Pozharskii AF. Handbook of Heterocyclic Chemistry   Elsevier; Oxford: 2000.  2nd ed.. p.91-140  
  • 3a Plaquevent J.-C. Levillain J. Guillen F. Malhiac C. Gaumont A.-C. Chem. Rev.  2008,  108:  5035 
    Suche in Google Scholar
  • 3b Martins MAP. Frizzo CP. Moreira DN. Zanatta N. Bonacorso HG. Chem. Rev.  2008,  108:  2015 
    Suche in Google Scholar
  • 3c Mlostoń G. Romański J. Jasiński M. Heimgartner H. Tetrahedron: Asymmetry  2009,  20:  1073 
    Suche in Google Scholar
  • 4a De Luca L. Curr. Med. Chem.  2006,  13:  1 
    Suche in Google Scholar
  • 4b Boiani M. González M. Mini-Rev. Med. Chem.  2005,  5:  409 
    Suche in Google Scholar
  • 5a Bureš F. Kulhánek J. Tetrahedron: Asymmetry  2005,  16:  1347 
    Suche in Google Scholar
  • 5b Bureš F. Szotkowski T. Kulhánek J. Pytela O. Ludwig M. Holčapek M. Tetrahedron: Asymmetry  2006,  17:  900 
    Suche in Google Scholar
  • 5c Sívek R. Pytela O. Bureš F. J. Heterocycl. Chem.  2008,  45:  1621 
    Suche in Google Scholar
  • 5d Sívek R. Pytela O. Kulhánek J. Bureš F. Molecules  2008,  13:  2326 
    Suche in Google Scholar
  • 5e Mucha P. Mlostoń G. Jasiński M. Linden A. Heimgarten H. Tetrahedron: Asymmetry  2008,  19:  1600 
    Suche in Google Scholar
  • 6 Kühl O. Chem. Soc. Rev.  2007,  36:  592 
    Suche in Google Scholar
  • 7a Kulhánek J. Bureš F. Pytela O. Mikysek T. Ludvík J. Rù˛ička A. Dyes Pigm.  2010,  85:  57 
    Suche in Google Scholar
  • 7b Bureš F. Kulhánek J. Mikysek T. Ludvík J. Lokaj J. Tetrahedron Lett.  2010,  51:  2055 
    Suche in Google Scholar
  • 8 Coppola GM. Schuster HF. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids   Wiley; New York: 1987. 
  • 9 Marek A. Kulhánek J. Ludwig M. Bureš F. Molecules  2007,  12:  1183 
    CrossrefPubMedSuche in Google Scholar
  • 10 Marek A. Kulhánek J. Bureš F. Synthesis  2009,  325 
    Thieme Connect
  • 11a Zhang XX. Brandshaw JS. Izatt RM. Chem. Rev.  1997,  97:  3313 
    Suche in Google Scholar
  • 11b Rajakumar P. Selvam SS. Dhanasekaran M. Tetrahedron Lett.  2005,  46:  6127 
    Suche in Google Scholar
  • 11c Galindo F. Becerril J. Burguete MI. Luis SV. Vigara L. Tetrahedron Lett.  2004,  45:  1659 
    Suche in Google Scholar
  • 11d Chen Y. Gao M. Tan S. Reibenspies JH. Zingaro RA. Heterocycles  2009,  78:  891 
    Suche in Google Scholar
  • 11e Rajakumar P. Srisailas M. Tetrahedron Lett.  2002,  43:  1909 
    Suche in Google Scholar
  • 12a You J.-S. Yu X.-Q. Zhang G.-L. Xiang Q.-X. Lan J.-B. Xie R.-G. Chem. Commun.  2001,  1816 
  • 12b Haberhauer G. Angew. Chem. Int. Ed.  2007,  46:  4397 
    Suche in Google Scholar
  • 13a Alcalde E. Mesquida N. Pérez-García L. Eur. J. Org. Chem.  2006,  3988 
  • 13b Alcade E. Alvarez-Rúa C. García-Granda S. García-Rodriguez E. Mesquida N. Pérez-García L. Chem. Commun.  1999,  295 
  • 13c Yuan Y. Gao G. Jiang Z.-L. You J.-S. Zhou Z.-Y. Yuan D.-Q. Xie R.-G. Tetrahedron  2002,  58:  8993 
    Suche in Google Scholar
  • 14a Rajakumar P. Rajhiman R. Selvam S. Rengasamy R. Nagaraj S. Bioorg. Med. Chem. Lett.  2009,  19:  3466 
    Suche in Google Scholar
  • 14b Rajakumar P. Sekar K. Shanmugaiah V. Mathivanan N. Bioorg. Med. Chem. Lett.  2008,  18:  4416 
    Suche in Google Scholar
  • 15a Baker MV. Brown DH. Simpson PV. Skelton BW. White AH. Dalton Trans.  2009,  7294 
  • 15b Barnard PJ. Baker MV. Bernes-Price SJ. Skelton BW. White AH. Dalton Trans.  2004,  1038 
  • 15c Baker MV. Brown DH. Haque RA. Skelton BW. White AH. Dalton Trans.  2004,  3756 
  • 15d Garrison JC. Simons RS. Talley JM. Tessier CA. Youngs WJ. Organometallics  2001,  20:  1276 
    Suche in Google Scholar
  • 15e Garrison J. Simons RS. Kofron WG. Tessier CA. Youngs WJ. Chem. Commun.  2001,  1780 
  • 15f Magill AM. McGuinness DS. Cavell KJ. Britovsek GJP. Gibson VC. White AJP. Williams DJ. White AH. Skelton BW. J. Organomet. Chem.  2001,  617-618:  546 
    Suche in Google Scholar
  • 16 Rajakumar P. Dhanasekaran M. Tetrahedron  2002,  58:  1355 
    CrossrefSuche in Google Scholar
  • 17a Baker MV. Bosnich MJ. Brown DH. Byrne LT. Hesler VJ. Skelton BW. White AH. Williams CC. J. Org. Chem.  2004,  69:  7640 
    Suche in Google Scholar
  • 17b Bitter I. Török Z. Csokai V. Grün A. Balázs B. Tóth G. Keserü GM. Kovári Z. Czugler M. Eur. J. Org. Chem.  2001,  2861 
18

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].