Chiral atropisomeric metalloporphyrins in the enantioselective styrene epoxidation

European Journal of Organic Chemistry

Volumn , Issue 7, 2000, Pages 1165-1171

  Reginato, Gloriana ^a   Di Bari, Lorenzo ^a   Salvadori, Piero ^a   Guilard, Roger ^b  

^a CNR   (Italy)

^b Lab d'Ingenierie Molec S   (France)

Author keywords

Asymmetric catalysis; Atropisomerism; Epoxidation; Porphyrinoids

Indexed keywords

METALLOPORPHYRIN; STYRENE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; EPOXIDATION; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0034058440     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200004)2000:7<1165::AID-EJOC1165>3.0.CO;2-8     Document Type: Article

References (43)

1. [1a] J. Fajer, Chem. Ind. 869-873 1991.
2. [1b] K. M. Smith, Porphyrins and Metalloporphyrins, Elsevier, Amsterdam, 1975.
3. [1c] G. M. Maggiora, L. L. Ingraham, Struct. Bonding, 1967, 2, 126-159.
4. [1d] M. Momenteau, C. A. Reed, Chem. Rev 1994, 94, 659-698.
5. [1e] B. G. Malmström, Acc. Chem. Res. 1993, 26, 332-338.
6. [1f] A. M. Stolzemberg, M T. Stershic, J. Am. Chem. Soc. 1988, 110, 6391-6402.
7. [2a] J. H. Dawson, M. Sono, Chem. Rev. 1987, 87, 1255-1276.
8. [2b] M. J. Gunter, P. Turner Coord. Chem. Rev. 1991, 108, 115-161.
9. [2c] Cytochrome P-450: Structure, Mechanism and Biochemistry (Ed: P. R. Ortiz de Montellano), Plenum Press, New York, 1986.
10. J. T. Groves, T. E. Nemo, R. S. Myers, J. Am. Chem. Soc. 1979, 101, 1032-1033.
11. [4a] J. T. Groves, W. J. Kruper Jr., R. C. Haushalter, J. Am. Chem. Soc. 1980, 102, 6375-6377.
12. [4b] G. T. Traylor, J. C. Marsters Jr., T. Nakano, B. E. Dunlap, J. Am. Chem. Soc. 1985, 107, 5537-5539.
13. [4c] J. P. Collman, T. Kodadek, S. A. Raybuck, B. Meunier, Proc. Natl. Acad. Sc. USA 1983, 80, 7039-7041.
14. [4d] J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792.
15. [4e] L. A. Campbell, T. Kodadek, J. Mol. Cat. A: Chemical 1996, 113, 293-310.
16. [4f] J. F. Barry, L. Campbell, D. W. Smith, T. Kodadek, Tetrahedron 1997, 53, 7753-7776.
17. [4g] Z. Gross, S. Ini, Inorg. Chem. 1999, 38, 1446-1449.
18. [5a] W. C. Lo, C. M. Che, K. F. Cheng, T. C. W. Mak, Chem. Commun. 1997, 1205-1206.
19. [5b] M. Frauenkron, A. Berkessel, Tetrahedron Lett. 1997, 38, 7175-7176.
20. [6a] J. A. Smegal, C. L. Hill, J. Am. Chem. Soc. 1983, 105, 3515-3521.
21. [6b] J. P. Collman, H. Tanaka, R. T. Hembre, J. L. Brauman, J. Am. Chem. Soc. 1990, 112, 3689-3690.
22. [7a] J. T. Groves, P. Viski, J. Org. Chem. 1990, 55, 3628-3634.
23. [7b] Y. Naruta, F. Tani, K. Maruyama, J. Chem. Soc., Chem. Commun. 1990, 1378-1380.
24. [7c] F. Pautet, M. Daudon, Tet. Lett. 1991, 32, 1457-1458.
25. [8a] S. O'Malley, T. Kodadek, J. Am. Chem. Soc. 1989, 111, 9116-9117.
26. [8b] J. L. Maxwell, S. O'Malley, K. C. Brown, T. Kodadek, Organometallics 1992, 11, 645-652.
27. J. P. Collman, Z. Wang, A. Straumanis, M. Quelquejeu, J. Am. Chem. Soc. 1999, 121, 460-461.
28. [10a] S. Matile, N. Berova, K. Nakanishi, S. Novkova, I. Philipova and B. Blagoev, J. Am. Chem. Soc. 1995, 117, 7021-7022.
29. [10b] S. Matile, N. Berova, K. Nakanishi, J. Fleischhauer and R.W. Woody, J. Am. Chem. Soc. 1996, 118, 5198-5206; S. Matile, N. Berova, K. Nakanishi, Enantiomer 1996, 1, 1-12.
30. [10b] S. Matile, N. Berova, K. Nakanishi, J. Fleischhauer and R.W. Woody, J. Am. Chem. Soc. 1996, 118, 5198-5206; S. Matile, N. Berova, K. Nakanishi, Enantiomer 1996, 1, 1-12.
31. H. Hotta, T. Suzuki, S. Miyano, Chem. Lett. 1990, 143-144.
32. K. E. Harding, L. M. May, K. F. Dick, J. Org. Chem. 1975. 40, 1664-1645.
33. [13a] J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney, A. M. Marguerettaz, J. Org. Chem. 1987, 52, 827-836.
34. [13b] J. S. Lindsey, R. W. Wagner, J. Org. Chem. 1989, 54, 828-836.
35. J. P. Collman, R. R. Gagne, C. A. Reed, T. R. Halbert, G. Lang, W. T. Robinson, J. Am. Chem. Soc. 1975, 97, 1427-1439.
36. Y. Naruta, F. Tani, N. Ishihara, K. Maruyama, J. Am. Chem. Soc. 1991, 113, 6865-6872.
37. [16a] H. H. Jaffé M. Orchin, Theory and Applications of Ultraviolet Spectroscopy, J. Wiley and Sons, New York, 1962.
38. [16b] A. Bree, T. Thirunamachandran, Mol. Phys. 1962, 5, 397-405.
39. [17a] J. E. Falk, Porphyrins and Metalloporphyrins, Elsevier, Amsterdam, 1964.
40. [17b] M. Gouterman, in The Porphyrins Vol. 3, Physical Chemistry, Part A (Ed.: D. Dolphin); Academic, New York, 1978.
41. [18a] L. J. Boucher, J. Am. Chem. Soc. 1968, 90, 6640-6645.
42. [18b] L. J. Boucher, J. Am. Chem. Soc. 1970, 92, 2725-2730.
43. H. Saltzman, J. G. Sharefkin, Org. Snth. 1963, 43, 60.