Induction of chirality into metal complexes by boronic acid-sugar interactions

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9473-9476

  Nuding, Guido ^a   Nakashima, Kazuaki ^a   Iguchi, Ritsuko ^a   Ishi i, Tsutomu ^a   Shinkai, Seiji ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER; IRON; METAL COMPLEX; SUGAR;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; ULTRASOUND THERAPY;

EID: 0032542143     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02148-0     Document Type: Article

References (24)

1. 1. a) Lehn, J.-M. Supramolecular Chemistry VCH, Weinheim 1995;
2. b) Zelewsky, A. V. Coordination Compounds in Supramolecutar Chemistry Wiley, Chichester 1996.
3. 2. a) Williams, A. Chem. Eur.J., 1997, 3, 15-16;
4. b) Constable, E. C.; Kulke, T.; Neuburger, M.; Zehnder, M. Chem. Commun., 1997, 489-490;
5. c) Charbonniere, L. J.; Williams, A. F.; Frey, U.; Merbach, A. E.; Kamalprija, P.; Schaad, O.J. Am. Chem. Soc., 1997, 119, 2488-2496.
6. 3. Newcome, G. R.; Moorefield, C.; Voegtle, F. Dendritic Molecules - Concepts*Synthesis*Perspectives VCH, Weinheim 1996.
7. 4. Chirality of 2,2′-bipyridine complexes can be influenced by a) terpene frameworks: Hayoz, P.; Zelewsky, A. V.; Stoeckli-Evans, H. J. Am. Chem. Soc., 1993, 115, 5111-5114;
8. b) boronic acid sugar template interaction: Mizuno, T.; Takeuchi, M.; Hamachi, I.; Nakashima, K.; Shinkai, S. Chem. Commun., 1997, 1793-1794;
9. c) amino acids: Weizman, H.; Libman, J.; Shanzer, A. J. Am. Chem. Soc., 1998, 120, 2188-2189.
10. 5. a) Lorand, J. P.; Edwards, J. D. J. Org. Chem., 1959, 24, 769-770;
11. b) James, T. D.; Sandanayake, S. K. R. A.; Shinkai, S. Nature, 1995, 374, 375.
12. 4 to receive 1, that was transformed to the amide 2; a similar connection is described by Yam, W.-W.; Kai, A.S.F. Chem. Commun., 1998, 109-110.
13. 4 to receive 1, that was transformed to the amide 2; a similar connection is described by Yam, W.-W.; Kai, A.S.F. Chem. Commun., 1998, 109-110.
14. 7. Precipitation occured mainly in form of gels; additional information about organic gelators: Yoza, K.; Ono, Y.; Yoshihara, K.; Akao, T.; Shinmori, H.; Takeuchi, M.; Shinkai, S. Reinhoudt, D.N. Chem. Commun., 1998, 109-110.
15. 8. 3 D,3 L, 4 D, 4 L, 5 D and 5L were characterized and assigned definitely and will be published in a full paper.
16. 9. a) Wood P. J.; Siddiqui, I. R. Carbohydr.Res., 1974, 32, 97-104;
17. b) Norrild, J.C.;Eggert, H.J.Am.Chem.Soc., 1995, 117, 1481-1484.
18. 10. Ishi-i, T.; Nakashima, K.; Shinkai, S. Tetrahedron, 1998, 54, 8679-8686.
19. 2 (X = SCN) were described by Driver, R.; Walker, W. R. Aust. J. Chem., 1967, 20, 1376-1383.
20. 12. Models were calculated with the Chem3D implanted MM2 module on a Mac Intosh Power PC.
21. 13. Hathaway, B. J.; Holah, D. G.; Postlethwaite, J. D. J. Chem. Soc., 1961, 3215-3218.
22. 14. a) Woods, C. R.; Benaglia, M.; Cozzi, F.; Siegel, J. S. Angew. Chem. Int. Ed. Engl., 1996, 35, 1830-1833;
23. b) Yamamoto, M.; Takeuchi, M.; Shinkai, S. Tetrahedron Lett., 1998, 39, 1189-1192;
24. c) Nabeshima, T.; Inaba, T.; Furukawa, N.; Hosoya, T.; Yano, Y. Inorg. Chem., 1993, 32, 1407-1416.