Evidence for substrate binding by the lanthanide centers in [Li 3(thf)n(binolate)3Ln]: Solution and solid-state characterization of seven- and eight-coordinate [Li3(sol) n(binolate)3Ln(S)m] adducts

Angewandte Chemie - International Edition

Volumn 45, Issue 16, 2006, Pages 2549-2552

  Wooten, Alfred J ^a   Carroll, Patrick J ^a   Walsh, Patrick J ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Asymmetric catalysis; Lanthanides; Lewis acids; Paramagnetic compounds; Reaction mechanisms

Indexed keywords

ASYMMETRIC CATALYSIS; LEWIS ACIDS; PARAMAGNETIC COMPOUNDS;

CHEMICAL BONDS; REACTION KINETICS; SOLUTIONS; SUBSTRATES;

RARE EARTH ELEMENTS;

CYCLOHEXANE; CYCLOHEXANE DERIVATIVE; LANTHANIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SOLUTION AND SOLUBILITY;

CYCLOHEXANES; LANTHANOID SERIES ELEMENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SOLUTIONS;

EID: 33746294798     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200504275     Document Type: Article

References (23)

1. H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura, M. Shibasaki, J. Am. Chem. Soc. 1993, 115, 10 372.
2. M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989.
3. M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187.
4. N. Yamagiwa, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 16 178.
5. H. C. Aspinall, J. F. Bickley, J. L. M. Dwyer, N. Greeves, R. V. Kelly, A. Steiner, Organometallics 2000, 19, 5416.
6. L. Di Bari, M. Lelli, G. Pintacuda, G. Pescitelli, F. Marchetti, P. Salvadori, J. Am. Chem. Soc. 2003, 125, 5549.
7. E. Takaoka, N. Yoshikawa, Y. M. A. Yamada, H. Sasai, M. Shibasaki, Heterocycles 1997, 46, 157.
8. H. Sasai, T. Arai, Y. Satow, K. N. Houk, M. Shibasaki, J. Am. Chem. Soc. 1995, 117, 6194.
9. H. C. Aspinall, Chem. Rev. 2002, 102, 1807.
10. A. F. Cockerill, G. L. O. Davies, R. C. Harden, D. M. Rackham, Chem. Rev. 1973, 73, 553.
11. Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942;
12. Angew. Chem. Int. Ed. Engl. 1997, 36, 1871.
13. W. D. Horrocks, J. P. Sipe, J. Am. Chem. Soc. 1971, 93, 6800.
14. H. Sasai, M. Bougauchi, T. Arai, M. Shibasaki, Tetrahedron Lett. 1997, 38, 2717.
15. T. Arai, Y. M. A. Yamada, N. Yamamoto, H. Sasai, M. Shibasaki, Chem. Eur. J. 1996, 2, 1368.
16. T. Morita, T. Arai, H. Sasai, M. Shibasaki, Tetrahedron: Asymmetry 1998, 9, 1445.
17. 2 = 0.1357, GoF = 1.035 (14 622 unique, nonzero reflections and 857 variables).
18. 2 = 0.1608, GoF = 1.151 (28 807 unique, nonzero reflections and 858 variables).
19. 2 = 0.0768, GoF = 1.082 (13 727 unique, nonzero reflections and 1064 variables). CCDC-284685, -284686, and -284687 (7, 8, 6, respectively) 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.
20. T. Kowall, F. Foglia, L. Helm, A. E. Merbach, J. Am. Chem. Soc. 1995, 117, 3790.
21. N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 4168.
22. N. Yoshikawa, T. Suzuki, M. Shibasaki, J. Org. Chem. 2002, 67, 2556.
23. N. Yamagiwa, J. Tian, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 3413.