Enantiomerically pure copper(II) cubanes [Cu4L 2(OMe)4] from chiral bis-1,3-diketones H2L through diastereoselective self-assembly

Angewandte Chemie - International Edition

Volumn 45, Issue 2, 2005, Pages 315-318

  Saalfrank, Rolf W ^a   Schmidt, Christine ^a   Maid, Harald ^a   Hampel, Frank ^a   Bauer, Walter ^a   Scheurer, Andreas ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Chirality; Copper; Cubanes; Oxo ligands; X ray diffraction

Indexed keywords

CARBOXYLIC ACIDS; CHEMICAL REACTIONS; MOLECULAR STRUCTURE; SELF ASSEMBLY; X RAY DIFFRACTION;

CHIRALITY; CUBANES; D-TARTARIC ACID; OXO-LIGANDS;

COPPER COMPOUNDS;

EID: 29544435510     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502477     Document Type: Article

References (49)

1. R. W. Saalfrank, H. Maid, N. Mooren, F. Hampel, Angew. Chem. 2002, 114, 323-326;
2. Angew. Chem. Int. Ed. 2002, 41, 304-307.
3. J. T. Adams, C. R. Hauser, J. Am. Chem. Soc. 1944, 66, 1220-1222;
4. R. Levine, J. A. Conroy, J. T. Adams, C. R. Hauser, J. Am. Chem. Soc. 1945, 67, 1510-1512.
5. For the description of the chirality of 7: see: M. F. Brown, B. R. Cook, T. E. Sloan, Inorg. Chem. 1975, 14, 1273-1278;
6. T. Damhus, C. E. Schäffer, Inorg. Chem. 1983, 22, 2406-2412;
7. A. von Zelewsky, Stereochemistry of Coordination Compounds, Wiley, Chichester, 1996, p. 70.
8. [14]
9. G. M. Sheldrick, C. Krüger, P. Goddard, Crystallographic Computing 3, Oxford University Press, Oxford 1985, p. 175;
10. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, 1997.
11. CCDC-253582 (7) and CCDC-275185 (ent-7) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
12. For asymmetric induction through stereogenic centers during self-assembly, see: O. Mamula, A. von Zelewsky, P. Brodard, C.-W. Schläpfer, G. Bernardinelli, H. Stoeckli-Evans, Chem. Eur. J. 2005, 11, 3049-3057;
13. H.-R. Tseng, S. A. Vignon, P. C. Celestre, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 2003, 9, 543-556;
14. G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, Chem. Eur. J. 1999, 5, 1862-1873;
15. E. J. Enemark, T. D. P. Stack, Angew. Chem. 1998, 110, 977-981;
16. Angew. Chem. Int. Ed. 1998, 37, 932-935.
17. For definition of diastereoselectivity, see: G. Helmchen, Enantiomer 1997, 2, 315-318.
18. J. K. Eberhardt, T. Glaser, R.-D. Hoffmann, R. Fröhlich, E.-U. Würthwein, Eur. J. Inorg. Chem. 2005, 1175-1181;
19. E. A. Buvaylo, V. N. Kokozay, O. Y. Vassilyeva, B. W. Skelton, J. Jezierska, L. C. Brunel, A. Ozarowski, Inorg. Chem. 2005, 44, 206-216;
20. A. Mukherjee, M. Nethaji, A. R. Chakravarty, Angew. Chem. 2004, 116, 89-92;
21. Angew. Chem. Int. Ed. 2004, 43, 87-90;
22. H. Oshio, Y. Saito, T. Ito, Angew. Chem. 1997, 109, 2789-2791;
23. Angew. Chem. Int. Ed. Engl. 1997, 36, 2673-2675;
24. J. Sletten, A. Sørensen, M. Juive, Y. Journaux, Inorg. Chem. 1990, 29, 5054-5058;
25. L. Schwabe, W. Haase, J. Chem. Soc. Dalton Trans. 1985, 1909-1913;
26. L. Merz, W. Haase, J. Chem. Soc. Dalton Trans. 1978, 1594-1598;
27. J. W. Hall, W. E. Estes, E. D. Estes, R. P. Scaringe, W. E. Hatfield, Inorg. Chem. 1977, 16, 1572-1574.
28. J. F. Berry, F. A. Cotton, C. Y. Liu, T. Lu, C. A. Murillo, B. S. Tsukerblat, D. Villagrán, X. Wang, J. Am. Chem. Soc. 2005, 127, 4895-4902;
29. G. Aromí, A. S. Batsanov, P. Christian, M. Helliwell, O. Roubeau, G. A. Timco, R. E. P. Winpenny, Dalton Trans. 2003, 4466-4471;
30. T. K. Paine, E. Rentschler, T. Weyhermüller, P. Chaudhuri, Eur. J. Inorg. Chem. 2003, 3167-3178;
31. E.-C. Yang, D. N. Hendrickson, W. Wernsdorfer, M. Nakano, L. N. Zakharov, R. D. Sommer, A. L. Rheingold, M. Ledezma-Gairaud, G. Christou, J. Appl. Phys. 2002, 91, 7382-7384;
32. H. Oshio, N. Hoshino, T. Ito, J. Am. Chem. Soc. 2000, 122, 12 602-12 603;
33. A. Escuer, M. Font-Bardía, S. B. Kumar, X. Solans, R. Vicente, Polyhedron 1999, 18, 909-914;
34. M. S. El Fallah, E. Rentschler, A. Caneschi, D. Gatteschi, Inorg. Chim. Acta 1996, 247, 231-235;
35. H.-J. Mai, R. Meyer zu Köcker, S. Wocadlo, W. Massa, K. Dehnicke, Angew. Chem. 1995, 107, 1349-1350;
36. Angew. Chem. Int. Ed. Engl. 1995, 34, 1235-1236;
37. M. A. Halcrow, J. C. Huffman, G. Christou, Angew. Chem. 1995, 107, 971-973;
38. Angew. Chem. Int. Ed. Engl. 1995, 34, 889-891;
39. K. L. Taft, A. Caneschi, L. E. Pence, C. D. Delfs, G. C. Papaefthymiou, S. J. Lippard, J. Am. Chem. Soc. 1993, 115, 11 753-11 766.
40. H. Imai, K. Inoue, K. Kikuchi, Y. Yoshida, M. Ito, T. Sunahara, S. Onaka, Angew. Chem. 2004, 116, 5736-5739;
41. Angew. Chem. Int. Ed. 2004, 43, 5618-5621;
42. R. Andrés, M. Brissard, M. Gruselle, C. Train, J. Vaissermann, B. Malézieux, J.-P. Jamet, M. Verdaguer, Inorg. Chem. 2001, 40, 4633-4640;
43. R. Andrés, B. Malézieux, M. Brissard, M. Gruselle, C. Train, M. Verdaguer, Chirality 2001, 13, 712-714;
44. G. L. J. A. Rikken, E. Raupach, Nature 2000, 405, 932-935;
45. G. L. J. A. Rikken, E. Raupach, Nature 1997, 390, 493-494.
46. (R,R) (ent-5) are consistent with a symmetrical AA′BB′CC′ six-spin system; see: A. Scheurer, H. Maid, F. Hampel, R. W. Saalfrank, L. Toupet, P. Mosset, R. Puchta, N. J. R. van Eikema Hommes, Eur. J. Org. Chem. 2005, 2566-2574;
47. A. Scheurer, P. Mosset, R. W. Saalfrank, Tetrahedron: Asymmetry 1999, 10, 3559-3570.
48. CD spectroscopic data of 5 and 7 were recorded in various solvents in the laboratory of Prof. M. Verdaguer (Université Pierre et Marie Curie at Paris, France). However, dichroism transitions above 400 nm, induced by the chirality of the metal centers of 7, could not be observed. Measurements below 400 nm were rendered impossible due to the strong absorption of ligand 5 in the range of wavelengths investigated.
49. H. D. Flack, Acta Crystallogr. Sect. A 1983, 39, 876-881.