Chiral confined space: Induction of stereochemistry in a M 4L4 metallosupramolecular container

Synthesis

Volumn , Issue 18, 2008, Pages 2963-2967

  Albrecht, Markus ^a   Burk, Simon ^a   Weis, Patrick ^b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Catechol; Chirality; Coordination compound; Self assembly; Tetrahedron

Indexed keywords

AMIDES; STEREOCHEMISTRY;

CATECHOL; CHIRALITY; COORDINATION COMPOUND; TETRAHEDRON;

SELF ASSEMBLY;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 53249121977     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067245     Document Type: Article

References (31)

1. (a) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, 1994.
2. (b) Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931.
3. (c) Helgeson, R. C.; Paek, K.; Knobler, C. B.; Maverick, E. F.; Cram, D. J. J. Am. Chem. Soc. 1996, 118, 5590.
4. (d) Sherman, J. C.; Cram, D. J. J. Am. Chem. Soc. 1989, 111, 4527.
5. (e) Beno, B. R.; Sheu, C.; Houk, K. N.; Warmuth, R.; Cram, D. J. Chem. Commun. 1998, 301.
6. (f) Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem. Int. Ed. 2004, 43, 6748;
7. Angew. Chem. 2004, 116, 6916.
8. (g) Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Science 2007, 316, 85.
9. (h) Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312, 251.
10. (i) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469.
11. (j) Grotzfeld, R. M.; Branda, N.; Rebek, J. Science 1996, 271, 487.
12. (k) Scarso, A.; Rebek, J. Jr. Top. Curr. Chem. 2006, 265, 1.
13. Enemark, E. J.; Stack, T. D. P. Angew. Chem. Int. Ed. 2004, 37, 932;
14. Angew. Chem. 1998, 110, 977.
15. (a) Terpin, A. J.; Ziegler, M.; Johnson, D. W.; Raymond, K. N. Angew. Chem. Int. Ed. 2004, 40, 157;
16. Angew. Chem. 2001, 113, 161.
17. (b) Davis, A. V.; Fiedler, D.; Ziegler, M.; Terpin, A.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 15354.
18. Argent, S. P.; Riis-Johannessen, T.; Jeffery, J. C.; Harding, L. P.; Ward, M. D. Chem. Commun. 2005, 4647.
19. (a) Albrecht, M.; Janser, I.; Meyer, S.; Weis, P.; Fröhlich, R. Chem. Commun. 2003, 2854.
20. (b) Albrecht, M.; Janser, I.; Burk, S.; Weis, P. Dalton Trans. 2006, 2875.
21. (c) Albrecht, M.; Burk, S.; Weis, P.; Schalley, C. A.; Kogej, M. Synthesis 2007, 3736.
22. See for comparison: (d) Amoroso, A. J.; Jefferey, J. C.; Jones, P. L.; McCleverty, J. A.; Thornton, P.; Ward, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1443;
23. Angew. Chem. 1995, 107, 1577.
24. (e) Brückner, C.; Powers, R. E.; Raymond, K. N. Angew. Chem. Int. Ed. 1998, 37, 1837;
25. Angew. Chem. 1998, 110, 1937.
26. (f) Saalfrank, R. W.; Glaser, H.; Demleitner, B.; Hampel, F.; Chowdhry, M. M.; Schünemann, V.; Trautwein, A. X.; Vaughan, G. B. M.; Yeh, R.; Davis, A. V.; Raymond, K. N. Chem. Eur. J. 2001, 8, 493.
27. Stack, T. D. P.; Karpishin, T. B.; Raymond, K. N. J. Am. Chem. Soc. 1992, 114, 1512.
28. Albrecht, M. Synlett 1996, 565.
29. Albrecht, M. Chem. Eur. J. 1997, 3, 1466.
30. Modelling Package, PC Spartan O2; Wavefunction Inc.: Irvine, 2002.
31. Albrecht, M.; Janser, I.; Fleischhauer, J.; Wang, Y.; Raabe, G.; Fröhlich, R. Mendeleev Commun. 2004, 250.