Design and synthesis of novel imidazolium-based ionic liquids with a pseudo crown-ether moiety: Diastereomeric interaction of a racemic ionic liquid with enantiopure europium complexes

Tetrahedron Letters

Volumn 45, Issue 51, 2004, Pages 9455-9459

  Ishida, Yasuhiro ^a   Sasaki, Daisuke ^a   Miyauchi, Hiroyuki ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Chiral recognition; Crown ether; Ionic liquid; Planar chirality

Indexed keywords

CROWN ETHER; CROWN ETHER DERIVATIVE; EUROPIUM; IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL BOND; COMPLEX FORMATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; LIQUID; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PROCESS DESIGN; ROOM TEMPERATURE; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 8844277654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.073     Document Type: Article

References (19)

1. For reviews, see: T. Welton Chem. Rev. 99 1999 2071
2. R. Sheldon Chem. Commun. 2001 2399
3. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772
4. T. Welton, and P. Wasserscheid Ionic Liquids in Synthesis 2003 Wiley-Interscience New York
5. For selected examples, see: A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes, and J.H. Davis Jr. J. Am. Chem. Soc. 124 2002 5962
6. S.T. Handy, M. Okello, C. Egrie, and G. Dickenson Proc. Electrochem. Soc. 19 2002 257
7. S.T. Handy, M. Okello, and G. Dickenson Org. Lett. 5 2003 2513
8. P. Wasserscheid, B. Drießen-Hölscher, R. van Hal, H.C. Steffens, and J. Zimmermann Chem. Commun. 2003 2038
9. Y. Ishida, H. Miyauchi, and K. Saigo Chem. Commun. 2002 2240
10. For examples of the investigations on the gauche effect in 1,4-dioxa systems, see: B. Ganguly, and B. Fuchs J. Org. Chem. 65 2000 558 and references cited therein
11. P. Bonhôte, A.-P. Dias, M. Armand, N. Papageorgiou, K. Kalyanasundaram, and M. Grätzel Inorg. Chem. 35 1996 1168
12. int = 0.0610. CCDC 242992 and CCDC 242993 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033
13. For examples of the lanthanoide-induced shifts of organic salts, see: T.J. Wenzel, and J. Zaia J. Org. Chem. 50 1985 1322 and references cited therein
14. K. Kabuto, and Y. Sasaki J. Chem. Soc., Chem. Commun. 1987 670
15. For examples of diastereomeric interactions of ionic liquids and chiral substrates, see: P. Wasserscheid, A. Bösmann, and C. Bolm Chem. Commun. 2002 200
16. Ref. 3
17. J. Levillain, G. Dubant, I. Abrunhosa, M. Gulea, and A.-C. Gaumont Chem. Commun. 2003 2914
18. H. Clavier, L. Boulanger, N. Audic, L. Toupet, M. Mauduit, and J.-C. Guillemin Chem. Commun. 2004 1224
19. J.J. Jodry, and K. Mikami Tetrahedron Lett. 45 2004 4429