Asymmetric heterogeneous catalysis by metalloporphyrins

Coordination Chemistry Reviews

Volumn 250, Issue 17-18, 2006, Pages 2212-2221

  Simonneaux, Gérard ^a   Le Maux, Paul ^a   Ferrand, Yann ^a   Rault Berthelot, Joelle ^a  

^a UMR 6509 Organometalliques et Catalyse Chimie et Electrochimie Moleculaires   (France)

Author keywords

Asymmetric; Heterogeneous catalysis; Porphyrins; Ruthenium

Indexed keywords

EID: 33746931779     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2006.01.014     Document Type: Review

References (95)

1. Leadbeater N.E., and Marco M. Chem. Rev. 102 (2002) 3217
2. McNamara C.A., Dixon M.J., and Bradley M. Chem. Rev. 102 (2002) 3275
3. Xia Q.H., Ge H.Q., Ye C.P., Liu Z.M., and Su K.X. Chem. Rev. 105 (2005) 1603
4. Fan Q.H., Li Y.M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385
5. Rechavi D., and Lemaire M. Chem. Rev. 102 (2002) 3467
6. Halterman R.L., and Jan S.T. J. Org. Chem. 56 (1991) 5253
7. Gross Z., Ini S., Kapon M., and Cohen S. Tetrahedron Lett. 37 (1996) 7325
8. Campbell L., and Kodadeck T. J. Mol. Catal. A: Chem. 113 (1996) 293
9. Simonneaux G., and Le Maux P. Coord. Chem. Rev. 228 (2002) 43
10. Che C.M., and Huang J.S. Coord. Chem. Rev. 231 (2002) 151
11. Berkessel A., Kaiser P., and Lex J. Chem. Eur. J. 9 (2003) 4746
12. Simonneaux G., and Tagliatesta P. J. Porphyrins Phtalocyanins 8 (2004) 1166
13. Leal O., Anderson D.L., Bowman R.G., Basolo F., and Burwell Jr. R.L. J. Am. Chem. Soc. 97 (1975) 5125
14. Battioni P., Lallier J.P., Barloy L., and Mansuy D. J. Chem. Soc, Chem. Commun. (1989) 1149
15. Nakamura M., Tatsumi T., and Tominaga H. Bull. Chem. Soc. Jpn. 63 (1990) 3334
16. Cooke P.R., and Linsay Smith J.R. Tetrahedron Lett. 33 (1992) 2737
17. Cooke P.R., and Lindsay Smith J.R. J. Chem. Soc, Perkin Trans. 1 (1994) 1913
18. Gilmartin C., and Lindsay Smith J.R. J. Chem. Soc., Perkin Trans 2 (1995) 243
19. Hilal H.S., Jondi W., Khalaf S., Keilani A., Suleiman M., and Schreiner A.F. J. Mol. Catal. A: Chem. 113 (1996) 35
20. Dores Assis M.D., and Lindsay Smith J.R. J. Chem. Soc., Perkin Trans. 2 (1998) 2221
21. Evans S.V., and Lindsay Smith J.R. J. Chem. Soc., Perkin Trans. 2 (2001) 174
22. Schiavon M.A., Iamamoto Y., Nascimento O.R., and Assis M.D. J. Mol. Catal. A: Chem. 174 (2001) 213
23. Liu C.J., Li S.G., Pang W.Q., and Che C.M. J. Chem. Soc., Chem. Commun. (1997) 65
24. Liu C.J., Yu W.Y., Li S.G., and Che C.M. J. Org. Chem. 63 (1998) 7364
25. Battioni P., Iwanejko R., Mansuy D., Mlodnicka T., Polowicz J., and Sanchez F. J. Mol. Catal. A: Chem. 109 (1996) 91
26. Bedioui F. Coord. Chem. Rev. 144 (1995) 39
27. Li Z., Xia C.G., and Zhang X.M. J. Mol. Catal. A: Chem. 185 (2002) 47
28. Cady S.S., and Pinnavaia T.J. Inorg. Chem. 17 (1978) 1501
29. Kameyama H., Suzuki H., and Amano A. Chem. Lett. (1988) 1117
30. Barloy L., Battioni P., and Mansuy D. J. Chem. Soc, Chem. Commun. (1990) 1365
31. Barloy L., Lallier J.P., Battioni P., Mansuy D., Piffard Y., Tournoux M., Valim J.B., and Jones W. N. J. Chem. 16 (1992) 71
32. Martinez-Lorente M.A., Battioni P., Kleemiss W., Bartoli J.F., and Mansuy D. J. Mol. Catal. A: Chem. 113 (1996) 343
33. Collman J.P., Ennis M.S., Offord D.A., Chang L.L., and Griffin J.H. Inorg. Chem. 35 (1996) 1751
34. Kim Y.H., Choi S.K., Park S.M., Nam W., and Kim S.J. Inorg. Chem. Commun. 5 (2002) 612
35. Deniaud D., Schöllorn B., Mansuy D., Rouxel J., Battioni P., and Bujoli B. Chem. Mater. 7 (1995) 995
36. Deniaud D., Spyroulias G.A., Bartoli J.F., Battioni P., Mansuy D., Pinel C., Odobel F., and Bujoli B. N. J. Chem. (1998) 901
37. Benitez I.O., Bujoli B., Camus L.J., Lee C.M., Odobel F., and Talham D.R. J. Am. Chem. Soc. 124 (2002) 4363
38. Anzenbacher J., and Kral P.V. J. Mol. Catal. A: Chem. 96 (1995) 311
39. Saito Y., Sartouchi M., Mifune M., Tai T., Odo J., Tanaka Y., Chikuma M., and Tanaka H. Bull. Chem. Soc. Jpn. 60 (1987) 2227
40. Labat G., and Meunier B. J. Org. Chem. 54 (1989) 5008
41. Leanord D.R., and Lindsay Smith J.R. J. Chem. Soc, Perkin Trans. 2 (1990) 1917
42. Leanord D.R., and Lindsay Smith J.R. J. Chem. Soc, Perkin Trans. 2 (1991) 25
43. Campestrini S., and Meunier B. Inorg. Chem. 31 (1992) 1999
44. Yu X.Q., Huang J.S., Yu W.Y., and Che C.M. J. Am. Chem. Soc. 122 (2000) 5337
45. van der Made A.W., Nolte S.J.W.H.R.J.M., and Drenth W. J. Chem. Soc., Chem. Commun. (1983) 1204
46. Mori T., Santa T., and Hirobe M. Tetrahedron Lett. 26 (1985) 5555
47. Higushi T., and Hirobe M. J. Mol. Catal. A: Chem. 113 (1996) 403
48. Geier III G.R., and Sazaki T. Tetrahedron 55 (1999) 1859
49. Geier III G.R., Lybrand T.P., and Sazaki T. Tetrahedron (1999) 1871
50. Traylor T.G., Byun Y.S., Traylor P.S., Battioni P., and Mansuy D. J. Am. Chem. Soc 113 (1991) 7821
51. Nestler O., and Severin K. Org. Lett. 3 (2001) 3907
52. Poriel C., Ferrand Y., Le Maux P., Paul C., Rault-Berthelot J., and Simonneaux G. Chem. Commun. (2003) 2308
53. Poriel C., Ferrand Y., Le Maux P., Rault-Berthelot J., and Simonneaux G. Inorg. Chem. 43 (2004) 5086
54. Zhang J.L., and Che C.M. Org. Lett. 4 (2002) 1911
55. Brulé E., and de Miguel Y.R. Tetrahedron Lett. 43 (2002) 8555
56. Benaglia M., Danelli T., and Pozzi G. Org. Biomol. Chem. 1 (2003) 454
57. Zhang J.L., Zhou H.B., Huang J.S., and Che C.M. Chem. Eur. J. 8 (2002) 1554
58. Che C.M., Huang J.S., and Zhang J.S. C.R. Chim. 6 (2003) 1105
59. Lai T.S., Kwong H.L., Zhang R., and Che C.M. J. Chem. Soc., Dalton Trans. (1998) 3559
60. Le Maux P., Bahri H., and Simonneaux G. J. Chem. Soc., Chem. Commun. (1991) 1350
61. Ini S., Kapon M., Cohen S., and Gross Z. Tetrahedron: Asymmetry 7 (1996) 659
62. Paul-Roth C., De Montigny F., Rethoré G., Simonneaux G., Gulea M., and Masson S. J. Mol. Catal. A: Chem. 201 (2003) 79
63. Ferrand Y., Le Maux P., and Simonneaux G. Org. Lett. 6 (2004) 3211
64. Che C.M., Huang J.S., Lee F.W., Li Y., Lai T.S., Kwong H.L., Teng P.F., Lee W.S., Lo W.C., Peng S.M., and Zhou Z.Y. J. Am. Chem. Soc. 123 (2001) 4119
65. Gross Z., Galili N., and Simkhovich L. Tetrahedron Lett. 40 (1999) 1571
66. Du G., Andrioletti B., Rose E., and Woo L.K. Organometallics 21 (2002) 4490
67. Li Y., Huang J.S., Zhou Z.Y., Che C.M., and You X.Z. J. Am. Chem. Soc. 124 (2002) 13185
68. Macor K.A., and Spiro T.G. J. Am. Chem. Soc. 105 (1983) 5601
69. Deronzier A., and Moutet J.C. Coord. Chem. Rev. 147 (1996) 339
70. Maruyama H., Segawa H., Sotoda S., Sato T., Kosai N., Sagisaka S., Shimidzu T., and Tanaka K. Synth. Met. 96 (1998) 141
71. Czuchajowski L., Bennett J.E., Goszczynski S., Wheeler D.E., Wisor A.K., and Malinski T. J. Am. Chem. Soc. 111 (1989) 607
72. Bedioui F., Devynck J., and Bied-Charreton C. Acc. Chem. Res. 28 (1995) 30
73. Ferrand Y., Poriel C., Le Maux P., Rault-Berthelot J., and Simonneaux G. Tetrahedron Asymmetry 16 (2005) 1463
74. Paul-Roth C., Rault-Berthelot J., and Simonneaux G. Tetrahedron 60 (2004) 12169
75. Poriel C., Ferrand Y., Juillard S., Le Maux P., and Simonneaux G. Tetrahedron 60 (2004) 145
76. Simonneaux G., Le Maux P., Ferrand Y., and Rault-Berthelot J. Adv. Coord. Bioinorg. Inorg. Chem. 7 (2005) 349
77. Svec F., and Fréchet J.M. Chem. Mater. 7 (1995) 707
78. Ferrand Y., Le Maux P., and Simonneaux G. Tetrahedron: Asymmetry 16 (2005) 3829
79. Felpin F.X., Doris E., Wagner A., Valleix A., Rousseau B., and Mioskowski C. J. Org. Chem. 66 (2001) 305
80. Zhang J.L., Liu Y.L., and Che C.M. Chem. Commun. (2002) 2906
81. Meunier B., de Visser S.P., and Shaik S. Chem. Rev. 104 (2004) 3947
82. Groves J.T., Shalyev K., and Lee J. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Pophyrin Handbook vol. 4 (2000), Academic Press, San Diego 17
83. Collman J.P., Wang Z., Straumanis A., Quelquejeu M., and Rose E. J. Am. Chem. Soc 121 (1999) 460
84. Rose E., Ren Q.Z., and Andrioletti B. Chem. Eur. J. 10 (2004) 224
85. Lai T.S., Zhang R., Cheung K.K., Kwong H.L., and Che C.M. J. Chem. Soc., Chem. Commun. (1998) 1583
86. Veyrat M., Maury O., Faverjon F., Over D.E., Ramasseul R., Marchon J.C., Turowska-Tyrk I., and Scheidt W.R. Angew. Chem., Int. Ed. Engl. 33 (1994) 220
87. Groves J.T., and Myers R.S. J. Am. Chem. Soc. 105 (1983) 5791
88. Zhang R., Yu W.Y., Wong K.Y., and Che C.M. J. Org. Chem. 66 (2001) 8145
89. Avnir D. Acc. Chem. Res. 28 (1995) 328
90. Köhn R., and Fröba M. Catal. Today 68 (2001) 227
91. Higushi T., Ohtake H., and Hirobe M. Tetrahedron Lett. 30 (1989) 6545
92. Burri E., Öhm M., Daguenet C., and Severin K. Chem. Eur. J. 11 (2005) 5055
93. Y. Ferrand, P. Le Maux, G. Simonneaux, unpublished results.
94. Bhyrappa P., Young J.K., Moore J.S., and Suslick K.S. J. Am. Chem. Soc. 118 (1996) 5708
95. Zhang J.L., Zhou H.B., Huang J.S., and Che C.M. Chem. Eur. J. 8 (2002) 1554