Enantiomeric epoxidation of 4-chlorostyrene with H2O2 catalysed by robust chloromanganese(III)-5,10,15,20-tetrakis-[2-chloro-6-(2,3,4,6- tetraacetyl-O-β-D-glucosyl)phenyl]porphyrins

Journal of Molecular Catalysis A: Chemical

Volumn 113, Issue 1-2, 1996, Pages 201-208

  Vilain Deshayes, Sandrine ^a   Maillard, Philippe ^a   Momenteau, Michel ^a  

^a INSTITUT CURIE   (France)

Author keywords

Alkenes; Asymmetric epoxidation; Chiral induction; Epoxidation; Glycosylated porphyrins; Porphyrins

Indexed keywords

EID: 0030602071     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(96)00056-8     Document Type: Article

References (27)

1. [1] P.R. Ortiz de Montellarto (Ed.), Cytochrome P-450: Structure, Mechanism and Biochemistry, Plenum Press, New York, (1986), p. 217-271.
2. [2] J.P. Collman, X. Zhang, V.J, Lee and J.I. Brauman, Science, 261 (1993) 1404-1411.
3. [3] Y. Naruta, in R.A. Sheldon (Ed.), Metalloporphyrins in Catalytic Oxidations, Marcel Dekker, New York, 1994, p. 241-259.
4. [4] J.P. Collman, V.J, Lee, C.J. Kellen-Yuen, X. Zhang, J.A. Ibers and J.I. Brauman, J. Am. Chem. Soc., 117 (1995) 692-703.
5. [5] B. Meunier, Chem. Rev., 92 (1992) 1411-1456.
6. [6] Ph. Maillard, J.-L. Guerquin-Kern, C. Huel and M. Momenteau, J. Org. Chem., 58 (1993) 2774-2780.
7. [7] Ph. Maillard, J.-L. Guerquin-Kern and M. Momenteau, Tetrahedron Lett., 32 (1991) 4901-4904.
8. [8] S. Vilain-Deshayes, A. Robert, Ph. Maillard, B. Meunier and M. Momenteau, J. Mol. Catal., (1996).
9. [9] C.K. Chang and F. Ebina, J. Chem. Soc., Chem. Commun., (1981) 778-779.
10. [10] P.S. Traylor, D. Dolphin and T.G. Traylor, J. Chem. Soc., Chem. Commun., (1984) 279-280.
11. [11] B. De Poorter and B. Meunier, Tetrahedron Lett., 25 (1984) 1895-1896.
12. [12] T.G. Traylor and S. Tsuchiya, Inorg. Chem., 26 (1987) 1338-1339.
13. [13] S. Tsuchiya and M. Seno, Chem. Lett., (1989) 263-268.
14. [14] P. Hoffman, A. Robert and B. Meunier, Bull. Soc. Chim. Fr., 129 (1992) 85-97.
15. [15] I. Artaud, K. Ben Aziza and D. Mansuy, J. Org. Chem., 58, (1993) 3373-3380.
16. [16] J.F. Bartoli, P. Battioni, W.R. De Poor and D. Mansuy, J. Chem. Soc., Chem. Commun., (1994) 23-24.
17. [17] S. Vilain, Ph. Maillard and M. Momenteau, J. Chem. Soc., Chem. Commun., (1994) 1697-1698.
18. [18] H. Turk and T.F. Warren, J. Org. Chem., 56 (1991) 1253-1260.
19. [19] P.L. Anelli, S. Banfi, F. Legramandi, F. Montanari, G. Pozzi and S. Quici, J. Chem. Soc., Perkin Trans. 1, (1993) 1345-1357.
20. [20] A.R. Adler, RR. Longo, F. Kampas and J. Kim, J. Inorg. Nucl. Chem., 32 (1970) 2443-2445.
21. [21] J.T. Groves and R.S. Myers, J. Am. Chem. Soc., 105 (1983) 5791-5796.
22. [22] S. Halazy, V. Berges, A. Ehrhard and C. Danzin, Bioorg. Chem., 18 (1990) 330-344.
23. [23] A.M.A. Rocha Gonsalves and M, Pereira, J. Heterocycl. Chem., 22, (1985) 931-933.
24. [24] J.S. Lindsey and R.W. Wagner, J. Org. Chem., 54 (1989) 828-836.
25. [25] Ph. Maillard, S. Vilain, C. Huel and M. Momenteau, J. Org. Chem., 59 (1994) 2887-2890.
26. [26] P.L. Anelli, S. Banfi, F. Montanari and S. Quici, J. Chem. Soc., Chem. Commun., (1989) 779-780.
27. [27] P. Battioni, J.P. Renaud, J.F. Bartoli, M. Reina-Artiles, M. Fort and D. Mansuy, J. Am. Chem. Soc., 110 (1988) 8462-8470.