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
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
3b
Martins MAP.
Frizzo CP.
Moreira DN.
Zanatta N.
Bonacorso HG.
Chem. Rev.
2008,
108:
2015
3c
Mlostoń G.
Romański J.
Jasiński M.
Heimgartner H.
Tetrahedron:
Asymmetry
2009,
20:
1073
4a
De Luca L.
Curr. Med. Chem.
2006,
13:
1
4b
Boiani M.
González M.
Mini-Rev. Med. Chem.
2005,
5:
409
5a
Bureš F.
Kulhánek J.
Tetrahedron: Asymmetry
2005,
16:
1347
5b
Bureš F.
Szotkowski T.
Kulhánek J.
Pytela O.
Ludwig M.
Holčapek M.
Tetrahedron: Asymmetry
2006,
17:
900
5c
Sívek R.
Pytela O.
Bureš F.
J. Heterocycl. Chem.
2008,
45:
1621
5d
Sívek R.
Pytela O.
Kulhánek J.
Bureš F.
Molecules
2008,
13:
2326
5e
Mucha P.
Mlostoń G.
Jasiński M.
Linden A.
Heimgarten H.
Tetrahedron: Asymmetry
2008,
19:
1600
6
Kühl O.
Chem.
Soc. Rev.
2007,
36:
592
7a
Kulhánek J.
Bureš F.
Pytela O.
Mikysek T.
Ludvík J.
Rù˛ička A.
Dyes Pigm.
2010,
85:
57
7b
Bureš F.
Kulhánek J.
Mikysek T.
Ludvík J.
Lokaj J.
Tetrahedron Lett.
2010,
51:
2055
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
10
Marek A.
Kulhánek J.
Bureš F.
Synthesis
2009,
325
11a
Zhang XX.
Brandshaw JS.
Izatt RM.
Chem.
Rev.
1997,
97:
3313
11b
Rajakumar P.
Selvam SS.
Dhanasekaran M.
Tetrahedron
Lett.
2005,
46:
6127
11c
Galindo F.
Becerril J.
Burguete MI.
Luis SV.
Vigara L.
Tetrahedron
Lett.
2004,
45:
1659
11d
Chen Y.
Gao M.
Tan S.
Reibenspies JH.
Zingaro RA.
Heterocycles
2009,
78:
891
11e
Rajakumar P.
Srisailas M.
Tetrahedron Lett.
2002,
43:
1909
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
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
14a
Rajakumar P.
Rajhiman R.
Selvam S.
Rengasamy R.
Nagaraj S.
Bioorg. Med. Chem. Lett.
2009,
19:
3466
14b
Rajakumar P.
Sekar K.
Shanmugaiah V.
Mathivanan N.
Bioorg. Med. Chem. Lett.
2008,
18:
4416
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
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
16
Rajakumar P.
Dhanasekaran M.
Tetrahedron
2002,
58:
1355
17a
Baker MV.
Bosnich MJ.
Brown DH.
Byrne LT.
Hesler VJ.
Skelton BW.
White AH.
Williams CC.
J.
Org. Chem.
2004,
69:
7640
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].