Enantiodiscrimination and enantiocontrol of neutral and cationic Pt II complexes bearing the Tropos biphep ligand: Application to asymmetric lewis acid catalysis

Angewandte Chemie - International Edition

Volumn 44, Issue 44, 2005, Pages 7257-7260

  Mikami, Koichi ^a   Kakuno, Hitomi ^a   Aikawa, Kohsuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Chirality; Diels Alder reaction; Enantioselectivity; Ene reaction; Platinum

Indexed keywords

CATALYSIS; ISOMERS; POSITIVE IONS; THERMAL EFFECTS;

CHIRALITY; DIELS-ALDER REACTION; ENANTIOSELECTIVITY; ENE REACTION;

PLATINUM COMPOUNDS;

EID: 27844506644     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502682     Document Type: Article

References (27)

1. a) E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis, Vol. 1-3, Springer, Berlin, 1999;
2. b) Transition Metals for Organic Synthesis (Eds. : M. Beller, C. Bolm), VCH, Weinheim, 1998;
3. c) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
4. d) H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis, VCH, Weinheim, 1993;
5. e) Catalytic Asymmetric Synthesis, Vol. I and II (Ed.: I. Ojima), VCH, New York, 1993, 2000.
6. K. Mikami, K. Aikawa, Y. Yusa, J. J. Jodry, M. Yamanaka, Synlett 2002, 10, 1561.
7. The activation barrier to axial torsion in selectively deuterated biphep is measured to be only (22 ± 1) kcal, which suggests that axial rotation takes place at room temperature or above: O. Desponds, M. Schlosser, Tetrahedron Lett. 1996, 37, 47.
8. a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517;
9. Angew. Chem. Int. Ed. 1999, 38, 495;
10. b) K. Mikami, K. Aikawa, T. Korenaga, Org. Lett. 2001, 3, 243;
11. c) T. Korenaga, K. Aikawa, M. Terada, S. Kawauchi, K. Mikami, Adv. Synth. Catal. 2001, 3, 284.
12. K. Mikami, S. Kataoka, Y. Yusa, K. Aikawa, Org. Lett. 2004, 6, 3699.
13. a) K. Mikami, K. Aikawa, Y. Yusa, M. Hatano, Org. Lett. 2002, 4, 91;
14. b) K. Mikami, K. Aikawa, Y. Yusa, Org. Lett. 2002, 4, 95.
15. For biphep-Pt complex: a) M. D. Tudor, J. J. Becker, P. S. White, M. R. Gagné, Organometallics 2000, 19, 4376;
16. b) J. J. Becker, P. S. White, M. R. Gagné, J. Am. Chem. Soc. 2001, 123, 9478. Use of different chirally flexible (tropos) nuphos ligands:
17. c) S. Doherty, C. R. Newman, R. K. Rath, H. Luo, M. Nieuwenhuyzen, J. G. Knight, Org. Lett. 2003, 5, 3863;
18. d) S. Doherty, J. K. Knight, C. Hardacre, H. Lou, C. R. Newman, R. K. Rath, S. Campbell, M. Nieuwenhuyzen, Organometallics 2004, 23, 6127.
19. K. Mikami, Y. Yusa, K. Aikawa, M. Hatano, Chirality 2003, 15, 105.
20. int = 0.082). R = 0.080, Rw = 0.171, goodness of fit = 0.993, and shift/error = 0.008. CCDC 277173 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.
21. M. Ogasawara, K. Yoshida, T. Hayashi, Organometallics 2000, 19, 1567.
22. a) M. Johannsen, K. A. Jørgensen, J. Org. Chem. 1995, 60, 5757;
23. b) M. Johannsen, K. A. Jørgensen, Tetrahedron 1996, 52, 7321;
24. c) S. Oi, K. Kashiwagi, E. Terada, K. Ohuchi, Y. Inoue, Tetrahedron Lett. 1996, 37, 6351;
25. d) S. Oi, E. Terada, K. Ohuchi, T. Kato, Y. Tachibana, Y. Inoue, J. Org. Chem. 1999, 64, 8660.
26. a) K. Aikawa, S. Kainuma, M. Hatano, K. Mikami, Tetrahedron Lett. 2004, 45, 183;
27. b) K. Mikami, K. Aikawa, S. Kainuma, Y. Kawakami, T. Saito, N. Sayo, H. Kumobayashi, Tetrahedron: Asymmetry 2004, 15, 3885.