Stereoselective coordination of C5-symmetric corannulene derivatives with an enantiomerically pure [RhI(nbd*)] metal complex

Angewandte Chemie - International Edition

Volumn 50, Issue 4, 2011, Pages 865-867

  Bandera, Davide ^a   Baldridge, Kim K ^a   Linden, Anthony ^a   Dorta, Reto ^a   Siegel, Jay S ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

corannulenes; dynamic NMR spectroscopy; metal arene complexes; stereochemistry

Indexed keywords

CORANNULENE DERIVATIVES; CORANNULENES; DYNAMIC NMR SPECTROSCOPY; ENANTIOPURE; QUANTUM MECHANICAL MODEL; STEREO-SELECTIVE; STEREOSELECTIVE RECOGNITION;

ENANTIOMERS; METAL COMPLEXES; METALS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY; RHODIUM; STEREOSELECTIVITY;

DYNAMICS;

CORANNULENE; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON; RHODIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; POLYCYCLIC HYDROCARBONS, AROMATIC; RHODIUM; STEREOISOMERISM;

EID: 78751565048     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006877     Document Type: Article

References (38)

1. W. S. Knowles, Angew. Chem. 2002, 114, 2096-2107
2. Angew. Chem. Int. Ed. 2002, 41, 1998-2027
3. R. Noyori, Angew. Chem. 2002, 114, 2108-2123
4. Angew. Chem. Int. Ed. 2002, 41, 2008-2022
5. K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135
6. Angew. Chem. Int. Ed. 2002, 41, 2024-2032.
7. L. Pauling, in The Nature of the Chemical Bond, Cornell University Press, Ithaca, 1960, pp. 564.
8. K. Mislow, M. Raban, in Topics in Stereochemistry, Vol. 1 (Eds.:, N. L. Allinger, E. L. Eliel,), Wiley, Hoboken, 1967, pp. 1-38.
9. P. Pfeiffer, K. Quehl, Ber. Dtsch. Chem. Ges. 1931, 64, 2667-2671
10. R. Noyori, M. Tokunaga, M. Kitamura, Bull. Chem. Soc. Jpn. 1995, 68, 36-56.
11. For reference studies on corannulene-metal complexation and dynamics, see
12. T. J. Seiders, K. K. Baldridge, J. M. O'Connor, J. S. Siegel, J. Am. Chem. Soc. 1997, 119, 4781-4782
13. J. S. Siegel, K. K. Baldridge, A. Linden, R. Dorta, J. Am. Chem. Soc. 2006, 128, 10644-10645.
14. S. Brydges, L. E. Harrington, M. J. McGlinchey, Coord. Chem. Rev. 2002, 233-234, 75-105
15. S. Brydges, N. Reginato, L. P. Cuffe, C. M. Seward, M. J. McGlinchey, C. R. Chim. 2005, 8, 1497-1505
16. T. G. Traylor, M. J. Goldberg, Organometallics 1987, 6, 2413-2416
17. T. G. Traylor, M. J. Goldberg, Organometallics 1987, 6, 2531-2536.
18. T. J. Seiders, E. L. Elliot, G. H. Grube, J. S. Siegel, J. Am. Chem. Soc. 1999, 121, 7804-7813
19. G. Grube, E. Elliot, R. Stephens, J. S. Siegel, Org. Lett. 2003, 5, 713-716.
20. Y. Sevryugina, A. Y. Rogachev, E. A. Jackson, L. T. Scott, M. A. Petrukhina, J. Org. Chem. 2006, 71, 6615-6618.
21. G. Berthon-Gelloz, T. Hayashi, J. Org. Chem. 2006, 71, 8957-8960.
22. 2D EXSY NMR=2D exchange NMR spectroscopy, for review see
23. C. L. Perrin, T. J. Dwyer, Chem. Rev. 1990, 90, 935-967
24. J. Sandström, Dynamic NMR Spectroscopy, Academic Press, New York, 1982.
25. CCDC-797434 (7) contains 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.
26. K. Mislow, Ann. N. Y. Acad. Sci. 1962, 93, 459-484, and references therein.
27. V. V. Bashilov, F. M. Dolgushin, P. V. Petrovskii, V. I. Sokolov, M. Sada, T. Benicori, G. Zotti, J. Organomet. Chem. 2005, 690, 4330-4336.
28. S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31
29. Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30.
30. A. K. Geim, K. S. Novoselov, Nat. Mater. 2007, 6, 183.
31. Truhlar/Zhang local module revision D.01 Gaussian 03, Gaussian Inc., Pittsburgh PA, 2003.
32. M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, S. T. Elbert, J. Comput. Chem. 1993, 14, 1347-1363.
33. Y. Zhao, D. G. Truhlar, J. Chem. Phys. 2006, 125, 1-18.
34. P. Fuentealba, H. Preuss, H. Stoll, L. von Szentpály, Chem. Phys. Lett. 1982, 89, 418-422.
35. J. M. L. Martin, A. Sundermann, J. Chem. Phys. 2001, 114, 3408-3420.
36. T. H. Dunning, J. Chem. Phys. 1989, 90, 1007-1023.
37. WEBMO: T. Cundari, J. R. Schmidt, www.webmo.net.
38. K. K. Baldridge, J. P. Greenberg, J. Mol. Graphics 1995, 13, 63-66.