Helical chirality in pentacoordinate zinc complexes - Selective access to both pseudoenantiomers with one ligand configuration

Angewandte Chemie - International Edition

Volumn 44, Issue 2, 2004, Pages 242-245

  Seitz, Michael ^a   Stempfhuber, Sabine ^a   Zabel, Manfred ^a   Schütz, Martin ^a,b   Reiser, Oliver ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Bisoxazoline ligands; Coordination chemistry; Helical chirality; Stereogenic metal centers; Zinc

Indexed keywords

CHIRALITY; HETEROATOMS; ZINC COMPLEXES;

IONS; SOLID STATE PHYSICS;

ZINC COMPOUNDS;

ZINC COMPLEX; LIGAND; ORGANOMETALLIC COMPOUND; OXAZOLE DERIVATIVE; ZINC;

ARTICLE; CHIRALITY; COMPLEX FORMATION; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; REACTION ANALYSIS; SYNTHESIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

LIGANDS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXAZOLES; STEREOISOMERISM; ZINC;

EID: 11844279120     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460843     Document Type: Article

References (36)

1. A. Werner, Ber. Dtsch. Chem. Ges. 1911, 44, 1887-1898.
2. Reviews: a) U. Knof, A. von Zelewsky, Angew. Chem. 1999, 111, 312-333; Angew. Chem. Int. Ed. 1999, 38, 302-322;
3. Reviews: a) U. Knof, A. von Zelewsky, Angew. Chem. 1999, 111, 312-333; Angew. Chem. Int. Ed. 1999, 38, 302-322;
4. b) H. Brunner, Angew. Chem. 1999, 111, 1248-1263; Angew. Chem. Int. Ed. 1999, 35, 1194-1208.
5. b) H. Brunner, Angew. Chem. 1999, 111, 1248-1263; Angew. Chem. Int. Ed. 1999, 35, 1194-1208.
6. For selected recent examples, see: a) C. Hamann. A. von Zelewsky, A. Neels, H. Stoeckli-Evans, Dalton Trans. 2004, 402-406;
7. b) H. Brunner, F. Henning, M. Weber, M. Zabel, D. Carmona, F. J. Lahoz, Synthesis 2003, 7, 1091-1099;
8. c) I. J. Munslow, A. J. Clarke, R. J. Deeth, I. Westmoreland, P. Scott, Chem. Commun. 2002, 1868-1869;
9. d) G. Muller, J. P. Riehl, K. J. Schenk, G. Hopfgartner, C. Piguet, J.-C. G. Bünzli, Eur. J. Inorg. Chem. 2002, 3101-3110;
10. e) G. Muller, J.-C. G. Bünzli, J. P. Riehl, D. Suhr, A. von Zelewsky, H. Mürner, Chem. Commun. 2002, 1522-1523;
11. f) D.-R. Ahn, T. W. Kim, J.-I. Hong, J. Org. Chem. 2001, 66, 5008-5011;
12. g) S. Fraysse, A. von Zelewsky, H. Stoeckli-Evans, New J. Chem. 2001, 5, 1374-1375;
13. h) R. S. Dickins, J. A. K. Howard, C. L. Maupin, J. M. Moloney, D. Parker, J. P. Riehl, G. Siligardi, J. A. G. Williams, Chem. Eur. J. 1999, 5, 1095-1105.
14. a) C. J. Sanders, P. N. O'Shaughnessy, P. Scott, Polyhedron 2003, 22, 1617-1625;
15. b) O. Mamula, A. von Zelewsky, T. Bark, H. Stoeckli-Evans, A. Neels, G. Bernardinelli, Chem. Eur. J. 2000, 6, 3575-3585;
16. c) L. Casella, M. E. Silver, J. A. Ibers, Inorg. Chem. 1984, 23, 1409-1418;
17. d) Y.-H. Chiu, O. dos Santos, J. W. Canary, Tetrahedron 1999, 55, 12069-12078;
18. e) A. Abufarag, H. Vahrenkamp, Inorg. Chem. 1995, 34, 3279-3284;
19. f) J. W. Canary, C. S. Allen, J. M. Castagnetto, Y. Wang, J. Am. Chem. Soc. 1995, 117, 8484-8485;
20. g) W. A. Nugent, R. L. Harlow, J. Am. Chem. Soc. 1994, 116, 6142-6148.
21. K. Bernauer, H. Stoeckli-Evans, D. Hugi-Cleary, H. J. Hilgers, H. Abd-el-Khalek, J. Porret, J.-J. Sauvain, Helv. Chim. Acta 1992, 75, 2327-2339.
22. M. Seitz, A. Kaiser, D. R. Powell, A. S. Borovik, O. Reiser, Adv. Synth. Catal. 2004, 346, 737-741.
23. M. Seitz, A. Kaiser, S. Stempfhuber, M. Zabel, O. Reiser, J. Am. Chem. Soc. 2004, 126, 11426-11427.
24. A. I. Meyers, W. Schmidt, M. J. McKennon, Synthesis, 1993, 250-262.
25. E. V. Dehmlow, J. Vor derBrüggen, J. Prakt. Chem. 2000, 342, 502-503.
26. B. Nock, H.-J. Pietsch, F. Tisato, T. Maina, P. Leibnitz, H. Spies, E. Chiotellis, Inorg. Chim. Acta 2000, 304, 26-32.
27. See Supporting Information.
28. 2-7a, single-point energy calculations were also performed with the TZVP basis set by Schäfer et al.[15e] in conjunction with the TZVP-MP2FITand TZVPPMP2FIT fitting basis sets,[15c] and an additional set of f functions with exponent 3.22 on the Zn center.
29. P. R. Bunker, P. Jensen, Molecular Symmetry and Spectroscopy, NRC Research, Ottawa, 1998.
30. R. B. Dyer, R. A. Palmer, R. G. Ghirardelli, J. S. Bradshaw, B. A. Jones, J. Am. Chem. Soc. 1987, 109, 4780-4786.
31. a) M. Schütz, H.-J. Werner, R. Lindh, F. R. Manby, J. Chem. Phys. 2004, 121, 737;
32. b) A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571;
33. c) F. Weigend, M. Häser, H. Patzelt, R. Ahlrichs, Chem. Phys. Lett. 1998, 294, 14;
34. d) M. Dolg, U. Wedig, H. Stoll, H. Preuss, J. Chem. Phys. 1987, 86, 866;
35. e) A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829.
36. CCDC-236253 and 236254 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+ 44) 1223-336-033; or deposit@ ccdc.cam.ac.uk).