Achiral and α-Amino Acid Derived Dicationic Imidazoliophanes

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.

cyclophanes - imidazoliophanes - amino acids - chiral pool - ligands

References

<A NAME="RZ09010SS-1">1</A> Gibson SE. Lecci C. Angew. Chem. Int. Ed.  2006,  45:  1364 

<A NAME="RZ09010SS-2">2</A> Katritzky AR. Pozharskii AF. Handbook of Heterocyclic Chemistry   Elsevier; Oxford: 2000.  2nd ed.. p.91-140  

<A NAME="RZ09010SS-3A">3a</A> Plaquevent J.-C. Levillain J. Guillen F. Malhiac C. Gaumont A.-C. Chem. Rev.  2008,  108:  5035 

<A NAME="RZ09010SS-3B">3b</A> Martins MAP. Frizzo CP. Moreira DN. Zanatta N. Bonacorso HG. Chem. Rev.  2008,  108:  2015 

<A NAME="RZ09010SS-3C">3c</A> Mlostoń G. Romański J. Jasiński M. Heimgartner H. Tetrahedron: Asymmetry  2009,  20:  1073 

<A NAME="RZ09010SS-4A">4a</A> De Luca L. Curr. Med. Chem.  2006,  13:  1 

<A NAME="RZ09010SS-4B">4b</A> Boiani M. González M. Mini-Rev. Med. Chem.  2005,  5:  409 

<A NAME="RZ09010SS-5A">5a</A> Bureš F. Kulhánek J. Tetrahedron: Asymmetry  2005,  16:  1347 

<A NAME="RZ09010SS-5B">5b</A> Bureš F. Szotkowski T. Kulhánek J. Pytela O. Ludwig M. Holčapek M. Tetrahedron: Asymmetry  2006,  17:  900 

<A NAME="RZ09010SS-5C">5c</A> Sívek R. Pytela O. Bureš F. J. Heterocycl. Chem.  2008,  45:  1621 

<A NAME="RZ09010SS-5D">5d</A> Sívek R. Pytela O. Kulhánek J. Bureš F. Molecules  2008,  13:  2326 

<A NAME="RZ09010SS-5E">5e</A> Mucha P. Mlostoń G. Jasiński M. Linden A. Heimgarten H. Tetrahedron: Asymmetry  2008,  19:  1600 

<A NAME="RZ09010SS-6">6</A> Kühl O. Chem. Soc. Rev.  2007,  36:  592 

<A NAME="RZ09010SS-7A">7a</A> Kulhánek J. Bureš F. Pytela O. Mikysek T. Ludvík J. Rù˛ička A. Dyes Pigm.  2010,  85:  57 

<A NAME="RZ09010SS-7B">7b</A> Bureš F. Kulhánek J. Mikysek T. Ludvík J. Lokaj J. Tetrahedron Lett.  2010,  51:  2055 

<A NAME="RZ09010SS-8">8</A> Coppola GM. Schuster HF. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids   Wiley; New York: 1987. 

<A NAME="RZ09010SS-9">9</A> Marek A. Kulhánek J. Ludwig M. Bureš F. Molecules  2007,  12:  1183 

<A NAME="RZ09010SS-10">10</A> Marek A. Kulhánek J. Bureš F. Synthesis  2009,  325 

<A NAME="RZ09010SS-11A">11a</A> Zhang XX. Brandshaw JS. Izatt RM. Chem. Rev.  1997,  97:  3313 

<A NAME="RZ09010SS-11B">11b</A> Rajakumar P. Selvam SS. Dhanasekaran M. Tetrahedron Lett.  2005,  46:  6127 

<A NAME="RZ09010SS-11C">11c</A> Galindo F. Becerril J. Burguete MI. Luis SV. Vigara L. Tetrahedron Lett.  2004,  45:  1659 

<A NAME="RZ09010SS-11D">11d</A> Chen Y. Gao M. Tan S. Reibenspies JH. Zingaro RA. Heterocycles  2009,  78:  891 

<A NAME="RZ09010SS-11E">11e</A> Rajakumar P. Srisailas M. Tetrahedron Lett.  2002,  43:  1909 

<A NAME="RZ09010SS-12A">12a</A> You J.-S. Yu X.-Q. Zhang G.-L. Xiang Q.-X. Lan J.-B. Xie R.-G. Chem. Commun.  2001,  1816 

<A NAME="RZ09010SS-12B">12b</A> Haberhauer G. Angew. Chem. Int. Ed.  2007,  46:  4397 

<A NAME="RZ09010SS-13A">13a</A> Alcalde E. Mesquida N. Pérez-García L. Eur. J. Org. Chem.  2006,  3988 

<A NAME="RZ09010SS-13B">13b</A> Alcade E. Alvarez-Rúa C. García-Granda S. García-Rodriguez E. Mesquida N. Pérez-García L. Chem. Commun.  1999,  295 

<A NAME="RZ09010SS-13C">13c</A> Yuan Y. Gao G. Jiang Z.-L. You J.-S. Zhou Z.-Y. Yuan D.-Q. Xie R.-G. Tetrahedron  2002,  58:  8993 

<A NAME="RZ09010SS-14A">14a</A> Rajakumar P. Rajhiman R. Selvam S. Rengasamy R. Nagaraj S. Bioorg. Med. Chem. Lett.  2009,  19:  3466 

<A NAME="RZ09010SS-14B">14b</A> Rajakumar P. Sekar K. Shanmugaiah V. Mathivanan N. Bioorg. Med. Chem. Lett.  2008,  18:  4416 

<A NAME="RZ09010SS-15A">15a</A> Baker MV. Brown DH. Simpson PV. Skelton BW. White AH. Dalton Trans.  2009,  7294 

<A NAME="RZ09010SS-15B">15b</A> Barnard PJ. Baker MV. Bernes-Price SJ. Skelton BW. White AH. Dalton Trans.  2004,  1038 

<A NAME="RZ09010SS-15C">15c</A> Baker MV. Brown DH. Haque RA. Skelton BW. White AH. Dalton Trans.  2004,  3756 

<A NAME="RZ09010SS-15D">15d</A> Garrison JC. Simons RS. Talley JM. Tessier CA. Youngs WJ. Organometallics  2001,  20:  1276 

<A NAME="RZ09010SS-15E">15e</A> Garrison J. Simons RS. Kofron WG. Tessier CA. Youngs WJ. Chem. Commun.  2001,  1780 

<A NAME="RZ09010SS-15F">15f</A> 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 

<A NAME="RZ09010SS-16">16</A> Rajakumar P. Dhanasekaran M. Tetrahedron  2002,  58:  1355 

<A NAME="RZ09010SS-17A">17a</A> Baker MV. Bosnich MJ. Brown DH. Byrne LT. Hesler VJ. Skelton BW. White AH. Williams CC. J. Org. Chem.  2004,  69:  7640 

<A NAME="RZ09010SS-17B">17b</A> Bitter I. Török Z. Csokai V. Grün A. Balázs B. Tóth G. Keserü GM. Kovári Z. Czugler M. Eur. J. Org. Chem.  2001,  2861 

<A NAME="RZ09010SS-18">18</A>

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: [phone], E-mail: [e-mail]].