Proline-modified porphyrin catalysts for enantioselective epoxidations: Design, synthesis, and reactivity

Helvetica Chimica Acta

Volumn 87, Issue 9, 2004, Pages 2447-2464

  Boitrel, Bernard ^a   Baveux Chambenoît, Valérie ^b   Richard, Philippe ^b  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; MOLECULES; OLEFINS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVE EPOXIDATION; ENANTIOSELECTIVITIES;

PORPHYRINS;

ALKENE; IRON; PORPHYRIN; PROLINE;

CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; EPOXIDATION; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

EID: 5644230882     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200490219     Document Type: Review

References (37)

1. 'Comprehensive Asymmetric Catalysis I-III'; Eds. E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer-Verlag, Berlin, Heidelberg, 1999.
2. R. Johnson, K. B. Sharpless, in 'Catalytic Asymmetric Synthesis', Ed. O. Iwao, Wiley-VCH, Weinheim, New York, 1993, p. 159.
3. E. N. Jacobsen, M. H. Wu, in 'Comprehensive Asymmetric Catalysis I-III'; Eds. E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer-Verlag, Berlin, Heidelberg, 1999; Vol. II, p. 649.
4. J. P. Collman, X. M. Zhang, V. J. Lee, E. S. Uffelman, J. I. Brauman, Science 1993, 261, 1404; E. Rose, A. Lecas, M. Quelquejeu, A. Kossanyi, B. Boitrel, Coord. Chem. Rev. 1998, 180, 1407; J.-L. Zhang, H.-B. Zhou, J.-S. Huang, C.-M. Che, Chem.-Eur. J. 2002, 8, 1554.
5. J. P. Collman, X. M. Zhang, V. J. Lee, E. S. Uffelman, J. I. Brauman, Science 1993, 261, 1404; E. Rose, A. Lecas, M. Quelquejeu, A. Kossanyi, B. Boitrel, Coord. Chem. Rev. 1998, 180, 1407; J.-L. Zhang, H.-B. Zhou, J.-S. Huang, C.-M. Che, Chem.-Eur. J. 2002, 8, 1554.
6. J. P. Collman, X. M. Zhang, V. J. Lee, E. S. Uffelman, J. I. Brauman, Science 1993, 261, 1404; E. Rose, A. Lecas, M. Quelquejeu, A. Kossanyi, B. Boitrel, Coord. Chem. Rev. 1998, 180, 1407; J.-L. Zhang, H.-B. Zhou, J.-S. Huang, C.-M. Che, Chem.-Eur. J. 2002, 8, 1554.
7. W. A. Nugent, T. V. RajanBabu, M. J. Burk, Science 1993, 259, 479; L. Deng, E. N. Jacobsen, J. Org. Chem. 1992, 57, 4320.
8. W. A. Nugent, T. V. RajanBabu, M. J. Burk, Science 1993, 259, 479; L. Deng, E. N. Jacobsen, J. Org. Chem. 1992, 57, 4320.
9. a) Z. Gross, S. Ini, J. Org. Chem. 1997, 62, 5514;
10. b) J. P. Collman, Z. Wang, A. Straumanis, M. Quelquejeu, E. Rose, J. Am. Chem. Soc. 1999, 121, 460;
11. c) E. Rose, M. Quelquejeu, R. P. Pandian, A. Lecas-Nawrocka, A. Vilar, G. Ricart, J. P. Collman, Z. Wang, A. Straumanis, Polyhedron 2000, 19, 581.
12. J. T. Groves, R. S. Myers, J. Am. Chem. Soc. 1983, 105, 5791.
13. R. L. Halterman, S.-T. Jan, J. Org. Chem. 1991, 56, 5253.
14. S. O'Malley, T. Kodadek, J. Am. Chem. Soc. 1989, 111, 9116; J. F. Barry, L. Campbell, D. W. Smith, T. Kodadek, Tetrahedron 1997, 53, 7753.
15. S. O'Malley, T. Kodadek, J. Am. Chem. Soc. 1989, 111, 9116; J. F. Barry, L. Campbell, D. W. Smith, T. Kodadek, Tetrahedron 1997, 53, 7753.
16. S. Vilain-Deshayes, A. Robert, P. Maillard, B. Meunier, M. Momenteau, J. Mol. Catal., A 1996, 113, 23.
17. G. Reginato, L. D. Bari, P. Salvadori, R. Guilard, Eur. J. Org. Chem. 2000, 1165.
18. a) D. Mansuy, P. Battioni, J.-P. Renaud, P. Guerin, J. Chem. Soc., Chem. Commun. 1985, 155;
19. b) J.-P. Renaud, P. Battioni, D. Mansuy, Nouv. J. Chim. 1987, 11, 279.
20. J. P. Collman, X. Zhang, V. J. Lee, J. I. Brauman, J. Chem. Soc., Chem. Commun. 1992, 1647; J. P. Collman, V. J. Lee, C. J. Kellenyuen, X. M. Zhang, J. A. Ibers, J. I. Brauman, J. Am. Chem. Soc. 1995, 117, 692.
21. J. P. Collman, X. Zhang, V. J. Lee, J. I. Brauman, J. Chem. Soc., Chem. Commun. 1992, 1647; J. P. Collman, V. J. Lee, C. J. Kellenyuen, X. M. Zhang, J. A. Ibers, J. I. Brauman, J. Am. Chem. Soc. 1995, 117, 692.
22. J. T. Groves, P. Viski, J. Org. Chem. 1990, 55, 3628.
23. a) B. Boitrel, A. Lecas, Z. Renko, E. Rose, New J. Chem. 1989, 13, 73;
24. b) B. Boitrel, A. Lecas, E. Rose, J. Chem. Soc., Chem. Commun. 1989, 349.
25. Y. Naruta, F. Tani, N. Ishihara, K. Maruyama, J. Am. Chem. Soc. 1991, 113, 6865.
26. Z. Gross, S. Ini, Inorg. Chem. 1999, 38, 1446.
27. L. C. Chiang, K. Konishi, T. Aida, S. Inoue, J. Chem. Soc., Chem. Commun. 1992, 254.
28. R. Zhang, W.-Y. Yu, T.-S. Lai, C.-M. Che, Chem. Commun. 1999, 409.
29. B. Boitrel, V. Baveux Chambenoît, P. Richard, Eur. J. Org. Chem. 2001, 4213.
30. B. Boitrel, V. Baveux Chambenoît, New J. Chem. 2003, 27, 942.
31. J. P. Collman, R. R. Gagne, C. A. Reed, T. R. Halbert, G. Lang, W. T. Robinson, J. Am. Chem. Soc. 1975, 97, 1427.
32. C. Pérollier, M. Mazzanti, J.-P. Simonato, F. Launay, R. Ramasseul, J.-C. Marchon, Eur. J. Org. Chem. 2000, 583.
33. P. Richard, E. Rose, B. Boitrel, Inorg. Chem. 1998, 37, 6532.
34. B. Boitrel, V Baveux-Chambenoît, P. Richard, Eur. J. Inorg. Chem. 2002, 1666.
35. E. Rose, M. Soleilhavoup, L. Christ-Tommasino, G. Moreau, J. P. Collman, M. Quelquejeu, A. Straumanis, J. Org. Chem. 1998, 63, 2042.
36. J. T. Groves, T. E. Nemo, J. Am. Chem. Soc. 1983, 705, 5786.
37. G. Reginato, Ph.D. Thesis, Università Degli Studi Di Pisa, Italy, 1995.