Synthesis of chiral Mn(III)-meso-tetrakis-[2.2]-p-cyclophanyl-porphyrin: A new catalyst for enantioselective epoxidation

Journal of Molecular Catalysis A: Chemical

Volumn 113, Issue 1-2, 1996, Pages 77-86

  Banfi, Stefano ^a   Manfredi, Amedea ^a   Montanari, Fernando ^a   Pozzi, Gianluca ^a   Quici, Silvio ^a  

^a CNR   (Italy)

Author keywords

2.2 p Cyclophane 4 carbaldehyde resolution; Asymmetric oxidation catalysts; Chiral complexes; Enantioselectivity; Epoxidation; Manganese; NaOCl epoxidation; Porphyrin

Indexed keywords

EID: 0030602002     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(96)00048-9     Document Type: Article

References (33)

1. [1] K.B. Sharpless, in B.M. Trost and I. Fleming Eds., Comprehensive Organic Synthesis, Vol. 7, Pergamon Press, New York, 1991, p. 389-436.
2. [2] J.P. Collmann, X. Zhang, V.J. Lee, E. Uffelman and J.I. Brauman, Science, 261 (1993) 1404.
3. [3] (a) E.N. Jacobsen, in J. Ojima Ed., Catalytic Asymmetric Synthesis, VCH, New York, 1993, p. 159-202;
4. (b) T. Katsuki, Coord. Chem. Rev., 140 (1995) 189-214.
5. [4] (a) E.N. Jacobsen, W. Zhang, A.R. Muci, J.R. Ecker and L. Ding, J. Am. Chem. Soc., 113 (1991) 7063;
6. (b) N.H. Lee, A.R. Muci and E.N. Jacobsen, Tetrahedron Lett., 32 (1991) 5055.
7. [5] (a) B. Meunier, Chem. Rev., 92 (1992) 1411-1456;
8. (b) S. Quici, S. Banfi and G. Pozzi, Gazz. Chim. Ital., 123 (1993) 597-612.
9. [6] J.T. Groves and R.S. Myers, J. Am. Chem. Soc., 105 (1983) 5791.
10. [7] T. Boschi, S. Licoccia, R. Paolesse, P. Tagliatesta in F. Montanari and L. Casella Eds., Metalloporphyrin Catalyzed Oxidations, Kluwer, Dordrecht, 1994, p. 239-267.
11. [8] S. O'Malley and T. Kodadek, J. Am. Chem. Soc., 111 (1989) 9116.
12. [9] R.L. Halterman and S.T. Jan, J. Org. Chem., 56 (1991) 5253.
13. [10] S.M. Rosenfeld and, P.M. Keehn Eds., The Cyclophanes, Vol. 1, 2, Academic Press, New York, 1983.
14. [11] (a) L. Czuchajowski and M. Lozynski, J. Heterocycl. Chem., 25 (1988) 349;
15. (b) L. Czuchajowski, S. Goszczynski, D.E. Weeler and A.K. Wisor, J. Heterocycl. Chem., 25 (1988) 1825.
16. [12] L. Czuchajowski, S. Goszczynski, A.K. Wisor, J.E. Bannett and T. Malinski, J. Heterocycl. Chem., 26 (1989) 1477;
17. (b) L. Czuchajowski, J.E. Bannett, S. Goszczynski, D.E. Wheeler, A.K. Wisor and T. Malinski, J. Am. Chem. Soc., 111 (1989) 607.
18. [13] L. Czuchajowski, S. Goszczynski and A.K. Wisor, Heterocycles, 29 (1989) 287.
19. [14] A. Rieche, H. Gross and E. Hoft, Chem. Ber., 93 (1960) 88.
20. [15] T. Izumi and T. Hinata, J. Chem. Technol. Biotechnol., 55 (1992) 227.
21. [16] D.Y. Antonov, Y.N. Belokon, N.S. Ikonnikov, S.A. Orlova, A.P. Pisarevsky, N.I. Raevsky, V.I. Rozemberg, E.V. Sergeeva, Y.T. Struchkov, V.I. Tararov and E.V. Vorontsov, J. Chem. Soc., Perkin Trans. 1, (1995) 1873.
22. [17] J.A. Dale, D.L. Dull and H.S. Mosher, J. Org. Chem., 34 (1969) 2543.
23. [18] J.S. Lindsey, I.C. Schreiman, H.C. Hsu, P.C. Kearney and A.M. Marguerettaz, J. Org. Chem., 52 (1987) 827.
24. [19] L. Czuchajowski, S. Goszczwnski and A.K. Wisor, J. Heterocycl. Chem., 25 (1985) 1343.
25. [20] P. Le Maux, H. Bahri and G. Simonneaux, Tetrahedron, 49 (1993) 1401.
26. [21] M.J. Crossley, L.D. Field, A.J. Foster, M.M. Harding and S. Sternhell, J. Am. Chem. Soc., 109 (1987) 341.
27. [22] (a) F. Montanari, M. Penso, S. Quici and P. Viganò, J. Org. Chem., 50 (1985) 4888;
28. (b) S. Banfi, F. Montanari and S. Quici, J. Org. Chem., 54 (1989) 1850;
29. (c) S. Banfi, M. Dragoni, F. Montanari, G. Pozzi and S. Quici, Gazz. Chim. Ital., 123 (1993) 431.
30. [23] G. Solladié, G. Demailly and C. Greck, Tetrahedron Lett., 62 (1985) 435.
31. [24] D.R. Boyd, D.M. Jerina and J.W. Daly, J. Org. Chem., 35 (1970) 3170.
32. [25] (a) A. Murano, Agr. Biol. Chem., 36 (1972) 2203;
33. (b) A. Murano, Agr. Biol. Chem., 37 (1973) 981.