Synthesis of a Chiral Alkyl-Bridged Bis(catecholamide) Ligand for the Self-Assembly of Enantiomerically Pure Helicates

Synlett

Volumn 1996, Issue 6, 1996, Pages 565-567

  Albrecht, Markus ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001880707     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5475     Document Type: Article

References (25)

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3. Lehn, J.-M. Supramolecular Chemistry, VCH: Weinheim, 1995. Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. Constable, E. C. Tetrahedron 1992, 48, 10013.
4. Lehn, J.-M. Supramolecular Chemistry, VCH: Weinheim, 1995. Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. Constable, E. C. Tetrahedron 1992, 48, 10013.
5. Lehn, J.-M. Supramolecular Chemistry, VCH: Weinheim, 1995. Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. Constable, E. C. Tetrahedron 1992, 48, 10013.
6. Krämer, R.; Lehn, J.-M.; De Cian, A.; Fischer, J. Angew. Chem. 1993, 105, 764; Angew. Chem. Int. Ed. Engl. 1993, 32, 703. Charbonniere, L. J.; Bernardinelli, G.; Piguet, C.; Sargeson, A. M.; Williams, A. F. J. Chem. Soc., Chem. Commun. 1994, 1419. Charbonniere, L. J.; Gilet, M.-F.; Bernauer, K.; Williams, A. F. J. Chem. Soc., Chem. Commun. 1996, 39.
7. Krämer, R.; Lehn, J.-M.; De Cian, A.; Fischer, J. Angew. Chem. 1993, 105, 764; Angew. Chem. Int. Ed. Engl. 1993, 32, 703. Charbonniere, L. J.; Bernardinelli, G.; Piguet, C.; Sargeson, A. M.; Williams, A. F. J. Chem. Soc., Chem. Commun. 1994, 1419. Charbonniere, L. J.; Gilet, M.-F.; Bernauer, K.; Williams, A. F. J. Chem. Soc., Chem. Commun. 1996, 39.
8. Krämer, R.; Lehn, J.-M.; De Cian, A.; Fischer, J. Angew. Chem. 1993, 105, 764; Angew. Chem. Int. Ed. Engl. 1993, 32, 703. Charbonniere, L. J.; Bernardinelli, G.; Piguet, C.; Sargeson, A. M.; Williams, A. F. J. Chem. Soc., Chem. Commun. 1994, 1419. Charbonniere, L. J.; Gilet, M.-F.; Bernauer, K.; Williams, A. F. J. Chem. Soc., Chem. Commun. 1996, 39.
9. Krämer, R.; Lehn, J.-M.; De Cian, A.; Fischer, J. Angew. Chem. 1993, 105, 764; Angew. Chem. Int. Ed. Engl. 1993, 32, 703. Charbonniere, L. J.; Bernardinelli, G.; Piguet, C.; Sargeson, A. M.; Williams, A. F. J. Chem. Soc., Chem. Commun. 1994, 1419. Charbonniere, L. J.; Gilet, M.-F.; Bernauer, K.; Williams, A. F. J. Chem. Soc., Chem. Commun. 1996, 39.
10. Zarges, W.; Hall, J.; Lehn, J.-M.; Bolm, C. Helv. Chim. Acta 1991, 74, 1843. Carrano, C. J.; Raymond, K. N. J. Am. Chem. Soc. 1978, 100, 5371. Corey, E. J.; Cywin, C. L.; Noe, M. C. Tetrahedron Lett. 1994, 35, 69. Enemark, E. J.; Stack, T. D. P. Angew. Chem. 1995, 107, 1082; Angew. Chem. Int. Ed. Engl. 1995, 34, 996.
11. Zarges, W.; Hall, J.; Lehn, J.-M.; Bolm, C. Helv. Chim. Acta 1991, 74, 1843. Carrano, C. J.; Raymond, K. N. J. Am. Chem. Soc. 1978, 100, 5371. Corey, E. J.; Cywin, C. L.; Noe, M. C. Tetrahedron Lett. 1994, 35, 69. Enemark, E. J.; Stack, T. D. P. Angew. Chem. 1995, 107, 1082; Angew. Chem. Int. Ed. Engl. 1995, 34, 996.
12. Zarges, W.; Hall, J.; Lehn, J.-M.; Bolm, C. Helv. Chim. Acta 1991, 74, 1843. Carrano, C. J.; Raymond, K. N. J. Am. Chem. Soc. 1978, 100, 5371. Corey, E. J.; Cywin, C. L.; Noe, M. C. Tetrahedron Lett. 1994, 35, 69. Enemark, E. J.; Stack, T. D. P. Angew. Chem. 1995, 107, 1082; Angew. Chem. Int. Ed. Engl. 1995, 34, 996.
13. Zarges, W.; Hall, J.; Lehn, J.-M.; Bolm, C. Helv. Chim. Acta 1991, 74, 1843. Carrano, C. J.; Raymond, K. N. J. Am. Chem. Soc. 1978, 100, 5371. Corey, E. J.; Cywin, C. L.; Noe, M. C. Tetrahedron Lett. 1994, 35, 69. Enemark, E. J.; Stack, T. D. P. Angew. Chem. 1995, 107, 1082; Angew. Chem. Int. Ed. Engl. 1995, 34, 996.
14. Zarges, W.; Hall, J.; Lehn, J.-M.; Bolm, C. Helv. Chim. Acta 1991, 74, 1843. Carrano, C. J.; Raymond, K. N. J. Am. Chem. Soc. 1978, 100, 5371. Corey, E. J.; Cywin, C. L.; Noe, M. C. Tetrahedron Lett. 1994, 35, 69. Enemark, E. J.; Stack, T. D. P. Angew. Chem. 1995, 107, 1082; Angew. Chem. Int. Ed. Engl. 1995, 34, 996.
15. Albrecht, M.; Kotila, S. Angew. Chem. accepted for publication Albrecht, M.; Röttele, H.; Burger, P. in preparation.
16. Albrecht, M.; Kotila, S. Angew. Chem. accepted for publication Albrecht, M.; Röttele, H.; Burger, P. in preparation.
17. Albrecht, M.; Kotila, S. Angew. Chem. 1995, 107, 2285; Angew. Chem. Int. Ed. Engl. 1995, 34, 2134.
18. Albrecht, M.; Kotila, S. Angew. Chem. 1995, 107, 2285; Angew. Chem. Int. Ed. Engl. 1995, 34, 2134.
19. Albrecht, M.; Riether, C. Chem. Ber. accepted for publication. Similar results were independently obtained: von Zelewsky, A.; Belser, P. personal communication, Nachbaur, J. A. PhD Thesis University of Fribourg (Switzerland) 1993.
20. Albrecht, M.; Riether, C. Chem. Ber. accepted for publication. Similar results were independently obtained: von Zelewsky, A.; Belser, P. personal communication, Nachbaur, J. A. PhD Thesis University of Fribourg (Switzerland) 1993.
21. Albrecht, M.; Riether, C. Chem. Ber. accepted for publication. Similar results were independently obtained: von Zelewsky, A.; Belser, P. personal communication, Nachbaur, J. A. PhD Thesis University of Fribourg (Switzerland) 1993.
22. Albrecht, M.; Franklin, S. J.; Raymond, K. N. Inorg. Chem. 1994, 33, 5785 and references cited therein. For chiral amide substituted monocatechol ligands and their metal complexes see: Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6115.
23. Albrecht, M.; Franklin, S. J.; Raymond, K. N. Inorg. Chem. 1994, 33, 5785 and references cited therein. For chiral amide substituted monocatechol ligands and their metal complexes see: Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6115.
24. Albrecht, M. Synthesis 1996, 230.
25. 2O: C 57.48, H 5.02, N 4.19; found: C 57.43, H 4.87, N 4.13.