Highly enantioselective olefin epoxidation controlled by helical confined environments

Journal of Catalysis

Volumn 309, Issue , 2014, Pages 21-32

  Fernandes, Cristina I ^a   Saraiva, Marta S ^a   Nunes, Teresa G ^b   Vaz, Pedro D ^a   Nunes, Carla D ^a  

^a UNIVERSITY OF LISBON   (Portugal)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

Asymmetric catalysis; Chiral recognition; Helical materials; Mesoporous materials; Molybdenum; Olefin epoxidation; Oxidation catalysis; Stereoselectivity

Indexed keywords

ASYMMETRIC CATALYSIS; CATALYTIC PRECURSORS; CHIRAL RECOGNITION; CONFINED ENVIRONMENT; OLEFIN EPOXIDATION; OXIDATION CATALYSIS; TERT-BUTYLHYDROPEROXIDE; TRANS-HEX-2-EN-1-OL;

CATALYSIS; CATALYSTS; MATERIALS; MOLYBDENUM; OLEFINS; STEREOSELECTIVITY; STYRENE;

MESOPOROUS MATERIALS;

EID: 84884684309     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2013.08.032     Document Type: Article

References (68)

1. A. Taguchi, and F. Schüth Micropor. Mesopor. Mater. 77 2005 1
2. M.H. Valkenberg, and W.F. Hölderich Catal. Rev. - Sci. Eng. 44 2002 321
3. F. Hoffmann, M. Cornelius, J. Morell, and M. Fröba Angew. Chem. Int. Ed. Engl. 45 2006 3216
4. T. Katsuki, and K.B. Sharpless J. Am. Chem. Soc. 102 1980 5974
5. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765
6. R. Irie, K. Noda, Y. Ito, N. Matsumoto, and T. Katsuki Tetrahedron Lett. 31 1990 7345
7. W. Zhang, J.L. Loebach, S.R. Wilson, and E.N. Jacobsen J. Am. Chem. Soc. 112 1990 2801
8. Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, and K.-X. Su Chem. Rev. 105 2005 1603
9. M. Shibasaki, H. Sasai, and T. Arai Angew. Chem. Int. Ed. Engl. 36 1997 1236
10. M.J. Porter, and J. Skidmore Chem. Commun. 2000 1215
11. D. Díez, M.G. Núñez, A.B. Antón, P. García, R.F. Moro, N.M. Garrido, I.S. Marcos, P. Basabe, and J.G. Urones Curr. Org. Synth. 5 2008 186
12. Y. Shi Acc. Chem. Res. 37 2004 488
13. M. Hickey, D. Goeddel, Z. Crane, and Y. Shi Proc. Natl. Acad. Sci. USA 101 2004 5794
14. S. Juliá, J. Masana, and J.C. Vega Angew. Chem. Int. Ed. Engl. 19 1980 929
15. S. Juliá, J. Guixer, J. Masana, J. Rocas, S. Colonna, R. Annuziata, and H. Molinari J. Chem. Soc. Perkin Trans. 1 1982 1317
16. J. Wang, L. Zhao, H. Shi, and J. He Angew. Chem. Int. Ed. Engl. 50 2011 9171
17. M.D. Jones, R. Raja, J.M. Thomas, B.F.G. Johnson, D.W. Lewis, J. Rouzaud, and K.D.M. Harris Angew. Chem. Int. Ed. Engl. 42 2003 4326
18. R. Raja, J.M. Thomas, M.D. Jones, B.F.G. Johnson, and D.E.W. Vaughan J. Am. Chem. Soc. 125 2003 14982
19. M.R. Castillo, L. Fousse, J.M. Fraile, J.I. García, and J.A. Mayoral Chem. Eur. J. 13 2007 287
20. J.M. Fraile, J.I. García, C.I. Herrerías, J.A. Mayoral, and M.A. Harmer J. Catal. 221 2004 532
21. J.M. Fraile, J.I. García, C.I. Herrerías, J.A. Mayoral, O. Reiser, A. Socullamos, and H. Werner Chem. Eur. J. 10 2004 2997
22. R.A. García, V. Morales, and T. Garcés J. Mater. Chem. 22 2012 2607
23. R.A. García, R. van Grieken, J. Iglesias, V. Morales, and N. Villajos J. Catal. 274 2010 221
24. T. Yamamoto, and M. Suginome Angew. Chem. Int. Ed. Engl. 48 2009 539
25. T. Yamamoto, T. Yamada, Y. Nagata, and M. Suginome J. Am. Chem. Soc. 132 2010 7899
26. T. Yamamoto, Y. Akai, Y. Nagata, and M. Suginome Angew. Chem. Int. Ed. Engl. 50 2011 8844
27. Y. Nagata, S. Ohashi, and M. Suginome J. Polym. Sci. Part A: Polym. Chem. 50 2012 1564
28. T. Gier, X. Bu, P. Feng, and G.D. Stucky Nature 395 1998 154
29. D. Bradshaw, T.J. Prior, E.J. Cussen, J.B. Claridge, and M.J. Rosseinsky J. Am. Chem. Soc. 126 2004 6106
30. A.E. Rowan, and R.J.M. Nolte Angew. Chem. Int. Ed. Engl. 37 1998 63
31. S. Che, Z. Liu, T. Ohsuna, K. Sakamoto, O. Terasaki, and T. Tatsumi Nature 429 2004 281
32. Y. Han, L. Zhao, and J.Y. Ying Adv. Mater. 19 2007 2454
33. D. Trong-On, D. Desplantier-Giscard, C. Danumah, and S. Kaliaguine Appl. Catal. A 222 2001 299
34. A.M. Balu, J.M. Hidalgo, J.M. Campelo, D. Luna, R. Luque, J.M. Marinas, and A.A. Romero J. Mol. Catal. A: Chem. 293 2008 17
35. N.U. Silva, C.I. Fernandes, T.G. Nunes, M.S. Saraiva, C.D. Nunes, and P.D. Vaz Appl. Catal. A 408 2011 105
36. N. Grover, and F.E. Kühn Curr. Org. Chem. 16 2012 16
37. M.R. Maurya Curr. Org. Chem. 16 2012 73
38. P.D. Vaz, and C.D. Nunes Curr. Org. Chem. 16 2012 89
39. C.D. Nunes, and P.D. Vaz A.C. Poehler, Homogeneous Catalysts: Types, Reactions and Applications 2011 Nova Science Publishers Inc. New York 43
40. A.J. Burke Coord. Chem. Rev. 252 2008 170
41. F.E. Kühn, A.M. Santos, and M. Abrantes Chem. Rev. 106 2006 2455
42. A.U. Barlan, A. Basak, and H. Yamamoto Angew. Chem. Int. Ed. Engl. 45 2006 5849
43. A.U. Barlan, W. Zhang, and H. Yamamoto Tetrahedron 63 2007 6075
44. N.U. Silva, T.G. Nunes, M.S. Saraiva, M.S. Shalamzari, P.D. Vaz, O.C. Monteiro, and C.D. Nunes Appl. Catal. B 113-114 2012 180
45. P.K. Baker Chem. Soc. Rev. 27 1998 125
46. W.M. Carmichael, D.A. Edwards, G.W.A. Fowles, and P.R. Marshall Inorg. Chem. Acta 1 1967 93
47. D. Betz, W.A. Herrmann, and F.E. Kühn J. Organomet. Chem. 694 2009 3320
48. N. Garelli, and P. Vierling J. Org. Chem. 57 1992 3046
49. M. Kruk, M. Jaroniec, and A. Sayari Langmuir 13 1997 6267
50. M. Kruk, V. Antochshuk, M. Jaroniec, and A. Sayari J. Phys. Chem. B 103 1999 10670
51. Z. Guo, Y. Du, Y. Chen, S.-C. Ng, and Y. Yang J. Phys. Chem. C 114 2010 14353
52. A.C. Ventura, C.I. Fernandes, M.S. Saraiva, T.G. Nunes, P.D. Vaz, and C.D. Nunes Curr. Inorg. Chem. 1 2011 156
53. B. Marler, U. Oberhagemann, S. Voltmann, and H. Gies Micropor. Mater. 6 1996 375
54. W. Hammond, E. Prouzet, S.D. Mahanti, and T.J. Pinnavaia Micropor. Mesopor. Mater. 27 1999 19
55. S.J. Gregg, and K.S.W. Sing Adsorption, Surface Area and Porosity second ed. 1982 Academic Press London
56. M.D. Alba, A. Becerro, and J. Klinowski J. Chem. Soc., Faraday Trans. 92 1996 849
57. A.A. Romero, M.D. Alba, W. Zhou, and J. Klinowski J. Phys. Chem. B 101 1997 5294 5300
58. M. Kruk, and M. Jaroniec Langmuir 15 1999 5410
59. P.D. Vaz, C.D. Nunes, M. Vasconcellos-Dias, M.M. Nolasco, P.J.A. Ribeiro-Claro, and M.J. Calhorda Chem. Eur. J. 13 2007 7874
60. W. Bett, and S. Cradoc Monatsh. Chem. 111 1980 193
61. J. Tang, L. Wang, G. Liu, Y. Liu, Y. Hou, W. Zhang, M. Jia, and W.R. Thiel J. Mol. Catal. A 313 2009 31
62. C.D. Nunes, A.A. Valente, M. Pillinger, A.C. Fernandes, C.C. Romão, J. Rocha, and I.S. Gonçalves J. Mater. Chem. 12 2002 1735
63. M. Vasconcellos-Dias, C.D. Nunes, P.D. Vaz, P. Ferreira, P. Brandão, V. Félix, and M.J. Calhorda J. Catal. 256 2008 301
64. M. Vasconcellos-Dias, S.R.M.M. de Aguiar, C.D. Nunes, P.D. Vaz, T.G. Nunes, and M.J. Calhorda Curr. Inorg. Chem. 1 2011 146
65. C.D. Nunes, A.A. Valente, M. Pillinger, J. Rocha, and I.S. Gonçalves Chem. Eur. J. 9 2003 4380
66. A. Galarneau, M. Nader, F. Guenneau, F. Di Renzo, and A. Gedeon J. Phys. Chem. C 111 2007 8268
67. A.I. Carrillo, E. Serrano, J.C. Serrano-Ruiz, R. Luque, and J. Garcia-Martinez Appl. Catal. A: Gen. 435-436 2012 1
68. A.I. Carrillo, E. Serrano, R. Luque, and J. Garcia-Martinez Chem. Commun. 46 2010 5163