Synthesis of chiral, amphiphilic, and water-soluble macrocycles via urea formation

Tetrahedron

Volumn 59, Issue 40, 2003, Pages 7921-7928

  Bhattacharyya, Tapes ^a   Sundin, Anders ^a   Nilsson, Ulf J ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

Macrocycle; Molecular recognition; Water soluble

Indexed keywords

ARGININE; ASPARTIC ACID; CARBONYL DERIVATIVE; DIAMINE DERIVATIVE; FORMIC ACID DERIVATIVE; GLUTAMIC ACID; GLYCINE; MACROCYCLIC COMPOUND; UREA; WATER;

ACYLATION; AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; CHIRALITY; PRIORITY JOURNAL; SOLUBILITY; SYNTHESIS;

EID: 0141852279     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.019     Document Type: Article

References (26)

1. Diederich F. Angew. Chem. Int. Ed. 27:1988;362-386.
2. Zhang X.X., Bradshaw J.S., Izatt R.M. Chem. Rev. 97:1997;3313-3361.
3. Davis A.P., Wareham R.S. Angew. Chem. Int. Ed. 38:1999;2978-2996.
4. Hartley J.H., James T.D., Ward C.J. J. Chem. Soc., Perkin Trans. 1. 2000;3155-3184.
5. Beer P.D., Gale P.A. Angew. Chem. Int. Ed. 40:2001;486-516.
6. Lavigne J.J., Anslyn E.V. Angew. Chem. Int. Ed. 40:2001;3118-3130.
7. Fitzmaurice R.J., Kyne G.M., Douheret D., Kilburn J.D. J. Chem. Soc., Perkin Trans. 1. 2002;841-864.
8. Hof F., Craig S.L., Nuckolls C., Rebek J. Jr. Angew. Chem. Int. Ed. 41:2002;1488-1508.
9. Davis A.M., Teague S.J. Angew. Chem. Int. Ed. Engl. 38:1999;736-749.
10. Lemieux R.U. Acc. Chem. Res. 29:1996;373-380.
11. Bhattacharyya T., Nilsson U. J. Tetrahedron Lett. 42:2001;2873-2875.
12. Kaplan L.J., Weisman G.R., Cram D.J. J. Org. Chem. 44:1979;2226-2233.
13. Stewart K.D., Miesch M., Knobler C.B., Maverick E.F., Cram D.J. J. Org. Chem. 51:1986;4327-4337.
14. Rosser M., Parker D., Ferguson G., Gallagher J.F., Howard J.A.K., Yufit D.S. Chem. Commun. 1993;1267-1269.
15. Cordier D., Coulet P.R. J. Chem. Soc., Perkin Trans. 2. 1994;891-894.
16. Cordier D., Dumaine-Bouaziz M., Coulet P.R. Anal. Lett. 28:1995;959-969.
17. Dave P.R., Doyle G., Axenrod T., Yazdekhasti H., Ammon H.L. J. Org. Chem. 60:1995;6946-6952.
18. Sharghi H., Niknam K., Massah A.R. J. Heterocycl. Chem. 36:1999;601-606.
19. Snellik-Ruel B.H.M., Antonisse M.M.G., Engbersen J.F.J., Timmerman P., Reinhoudt D.N., Eur. J. Org. Chem. 2000;165-170.
20. Tejeda A., Oliva A.I., Simón L., Grande M., Caballero M.C., Morán J.R. Tetrahedron Lett. 41:2000;4563-4566.
21. Bell T.W., Khasanov A.B., Drew M.G.B., Filikov A., James T.L. Angew. Chem. Int. Ed. 38:1999;2543-2547.
22. Douteau-Guével N., Coleman A.W., Morel J.-P., Morel-Desrosiers N. J. Chem. Soc., Perkin Trans. 2. 1999;629-633.
23. Kazakova E.K., Makarova N.A., Ziganshina A.U., Muslinkina L.A., Muslinkin A.A., Habicher W.D. Tetrahedron Lett. 41:2000;10111-10115.
24. Welti R., Diedrich F. Helv. Chim. Acta. 86:2003;494-503.
25. Thompson S.E., Smithrud D.B. J. Am. Chem. Soc. 124:2002;442-449.
26. Wilcox C.S. Schneider H.-J., Dürr H. Frontiers in Supramolecular Organic Chemistry and Photochemistry. 1990;123-143 VCH, Weinheim.