X=Y-ZH systems as potential 1,3-dipoles. Part 61: Metal exchanged zeolites, silver(I) oxide, Ni(II) and Cu(I) complexes as catalysts for 1,3-dipolar cycloaddition reactions of imines generating proline derivatives

Tetrahedron

Volumn 61, Issue 36, 2005, Pages 8677-8685

  Grigg, Ronald ^a   Cooper, Daniel M ^a   Holloway, Stephen ^b   McDonald, Simon ^b   Millington, Emma ^a   Sarker, Mohammed A B ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Cu(I) catalysis; Cycloaddition; Metallo azomethine ylides; Ni(II) catalysis; Silver oxide; Silver exchanged zeolites

Indexed keywords

COPPER COMPLEX; IMINE; NICKEL COMPLEX; PROLINE DERIVATIVE; SILVER DERIVATIVE; TITANIUM DIOXIDE; ZEOLITE;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 23444432465     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.06.110     Document Type: Article

References (78)

1. Y. Li, and J.N. Armor Appl. Catal., B 2 1993 239 256
2. Z. Li, and M. Flytzani-Stephanopoulos Appl. Catal., A 165 1997 15 34
3. M. Matsuoka, W.-S. Ju, and M. Anpo Chem. Lett. 2000 626 627
4. J.W. Teng, T.X. Cai, and X.H. Bao Chin. Chem. Lett. 10 1999 83 86
5. J.A. Martens, A. Cauvel, A. Francis, C. Hermans, F. Jayat, M. Remy, M. Keung, J. Lievens, and P.A. Jacobs Angew. Chem., Int. Ed. 37 1998 1901 1903
6. D.K. Murray, T. Howard, P.W. Goguen, T.R. Krawietz, and J.F. Haw J. Am. Chem. Soc. 116 1994 6354 6360
7. S. Chatterjee, H.L. Greene, and Y.J. Park J. Catal. 138 1992 179 194
8. G. Bagnasco, P. Ciamgelli, E. Czaran, J. Rapp, and G. Russo Metal Microstrutures in Zeolites 1982 Elsevier Amsterdam
9. M. Nomura, and Y. Fujihara Chem. Express 7 1992 121 124
10. G.A. Ozin, and F. Hugues J. Phys. Chem. 86 1982 5174 5179
11. G.A. Ozin, F. Hugues, S.M. Matta, and D.F. McIntosh J. Phys. Chem. 87 1983 3445 3450
12. R.L. Thomas, A.K. Sarker, K. Kohata, S.A. Abbas, and K. Matta Tetrahedron Lett. 31 1990 2825 2828
13. M.A. Probert, J. Zhang, and D.R. Bundle Carbohydrate Res. 296 1996 149 170
14. J. Zhang, A. Otter, and D.R. Bundle Bioorg. Med. Chem. 4 1996 1989 2001
15. P.J. Garegg, C. Henrichson, T. Norberg, and P. Ossowski Carbohydrate Res. 119 1983 95 100
16. R. Grigg, H.Q.N. Gunaratne, and V. Sridharan Tetrahedron 43 1987 5887 5898
17. R. Grigg, and V. Sridharan Adv. Cycloaddition 3 1993 161 204
18. D.A. Barr, R. Grigg, and V. Sridharan Tetrahedron Lett. 30 1989 4727 4730
19. P. Allway, and R. Grigg Tetrahedron Lett. 32 1991 5817 5820
20. R. Grigg Tetrahedron: Asymmetry 6 1995 2475 2486
21. J.M. Longmire, B. Wang, and X. Zhang J. Am. Chem. Soc. 124 2002 13400 13401
22. K.V. Gothelf, R.G. Hazell, and K.A. Jorgensen Angew. Chem., Int. Ed. 41 2002 4236 4238
23. Y. Oderaotoshi, W. Cheng, S. Fujitomi, Y. Kasano, S. Minakata, and M. Komatsu Org. Lett. 5 2003 5043 5046
24. C. Chen, X. Li, and S.L. Schreiber J. Am. Chem. Soc. 125 2003 10174 10175
25. D.A. Barr, M.J. Dorrity, R. Grigg, J.F. Malone, J. Montgomery, S. Rajviroongit, and P. Stevenson Tetrahedron Lett. 31 1990 6569 6572
26. D.M. Cooper, R. Grigg, S. Hargreaves, P. Kennewell, and J. Redpath Tetrahedron 51 1995 7791 7808
27. D.A. Barr, M.J. Dorrity, R. Grigg, S. Hargreaves, J.F. Malone, J. Montgomery, J. Redpath, P. Stevenson, and M. Thornton-Pett Tetrahedron 51 1995 273 294
28. T. Coulter, R. Grigg, J.F. Malone, and V. Sridharan Tetrahedron Lett. 32 1991 5417 5420
29. R. Grigg, V. Sridharan, S. Suganthan, and A.W. Bridge Tetrahedron 51 1995 295 306
30. R. Grigg, Z. Rankovic, M. Thornton-Pett, and A. Somasunderam Tetrahedron 49 1993 8679 8690
31. R. Grigg, M. Thornton-Pett, and G. Yoganathan Tetrahedron 55 1999 8129 8140
32. S.G. Pyne, J. Safaei, A.K. Schafer, A. Javidan, B.W. Skelton, and A.H. White Aust. J. Chem. 51 1998 137 158
33. S.G. Pyne, J. Safaei-G, and F. Koller Tetrahedron Lett. 36 1995 2511 2514
34. S.G. Pyne, B. Dikic, P. Gordon, B.W. Skelton, and A.H. White Aust. J. Chem. 46 1993 73 93
35. H. Waldmann, E. Blaeser, M. Jansen, and H.P. Letschert Angew. Chem., Int. Ed. Engl. 106 1994 717 719
36. H. Waldmann, E. Blaeser, M. Jansen, and H.-P. Letschert Chem. Eur. J. 1 1995 150 154
37. R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, and T. Pilati Tetrahedron: Asymmetry 2 1991 1329 1342
38. G. Galley, J. Liebscher, and M. Paetzel J. Org. Chem. 60 1995 5005 5010
39. M. Patzel, G. Galley, P.G. Jones, and A. Chrapkowsky Tetrahedron Lett. 34 1993 5707 5710
40. J.L. Garcia Ruano, A. Tito, and M.T. Peromingo J. Org. Chem. 67 2002 981 987
41. A. Viso, R. Fernandez de la Pradilla, C. Guerrero-Strachan, M. Alonso, M. Martinez-Ripoll, and I. Andre J. Org. Chem. 62 1997 2316 2317
42. M.M. Murphy, J.R. Schullek, E.M. Gordon, and M.A. Gallop J. Am. Chem. Soc. 117 1995 7029 7030
43. S.P. Hollinshead Tetrahedron Lett. 37 1996 9157 9160
44. M.A. Marx, A.-L. Grillot, C.T. Louer, K.A. Beaver, and P.A. Bartlett J. Am. Chem. Soc. 119 1997 6153 6167
45. Y.D. Gong, S. Najdi, M.M. Olmstead, and M.J. Kurth J. Org. Chem. 63 1998 3081 3086
46. G. Peng, A. Sohn, and M.A. Gallop J. Org. Chem. 64 1999 8342 8349
47. H.A. Dondas, R. Grigg, W.S. MacLachlan, D.T. MacPherson, J. Markandu, V. Sridharan, and S. Suganthan Tetrahedron Lett. 41 2000 967 970
48. G. Burton, T.W. Ku, T.K. Carr, T. Kiesow, R.T. Sarisky, J. Lin-Goerke, A. Baker, D.L. Earnshaw, G.A. Hofmann, R.M. Keenan, and D. Dhanak Bioorg. Med. Chem. Lett. 15 2005 1553 1556
49. A. Zubia, L. Mendoza, S. Vivanco, E. Aldaba, T. Carrascal, B. Lecea, A. Arrieta, T. Zimmerman, F. Vidal-Vanaclocha, and F.P. Cossio Angew. Chem., Int. Ed. 44 2005 2903 2907
50. R.J. Booth, and J.C. Hodges Acc. Chem. Res. 32 1999 18 26
51. U. Grabowska, A. Rizzo, K. Farnell, and M. Quibell J. Comb. Chem. 2 2000 475 490
52. S.V. Ley, and A. Massi J. Comb. Chem. 2 2000 104 107
53. A. Golisade, J.C. Bressi, C.S. Van, M.H. Gelb, and A. Link J. Comb. Chem. 2 2000 537 544
54. S. Bhattacharyya Comb. Chem. High Throughout Screen. 3 2000 65 92
55. Commercial 100-mesh silver exchanged zeolite contains 20% Ag (Aldrich) and 1 mol equiv Ag was used in the reaction.
56. Y. Kim, and K. Seff J. Phys. Chem. 82 1978 925 929
57. G. Consiglio, and A. Indolese J. Organomet. Chem. 463 1993 23 27
58. G. Consiglio, and A. Indolese Organometallics 10 1991 3425 3427
59. E. Griswold, J. Kleinberg, and R.H. Lee Inorg. Chem. 3 1964 1278 1283
60. L.M. Venanzi J. Chem. Soc. 1958 719 724
61. A. Chakravorty, G.W. Everett, and R.H. Holm Prog. Inorg. Chem. 7 1966 83 214
62. G.R. van Hecke, and W.D. Horrocks Inorg. Chem. 5 1966 1968 1974
63. G. Consiglio, F. Morandini, and O. Piccolo Inorg. Chim. Acta 57 1982 15 19
64. C.P. Kubiak E.W. Abel F.G.A. Stone G. Wilkinson Comprehensive Organometallic Chemistry II Vol. 9 1995 Pergamon New York 1 14
65. D. Nicholls A.F. Trotman-Dickenson Comprehensive Inorganic Chemistry Vol. 3 1975 Pergamon 1109
66. D.A. Barr, R. Grigg, H.Q.N. Gunaratne, J. Kemp, P. McMeekin, and V. Sridharan Tetrahedron 44 1988 557 570
67. R. Grigg, J. Kemp, J.F. Malone, S. Rajviroongit, and A. Tangthongkum Tetrahedron 44 1988 5361 5374
68. G. Sekar, A. DattaGupta, and V.K. Singh J. Org. Chem. 63 1998 2961 2967
69. M. Kanai, and K. Tomioka Tetrahedron Lett. 36 1995 4275 4278
70. X. Li, J. Yang, and M.C. Kozlowski Org. Lett. 3 2001 1137 1140
71. K. Sonogashira B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 3 1991 Pergamon New York 521 549
72. C. Janiak, L. Vehlin, H.-P. Wu, P. Klufers, H. Piotrowski, and T.G. Sharmann J. Chem. Soc., Dalton Trans. 1999 3121 3131
73. L.I. Victoriano, M.T. Garkand, A. Vega, and C. Lopez Inorg. Chem. 37 1998 2060 2062
74. P. Alemany, L. Bengtsson-Kloo, and B. Holmberg Acta Chem. Scand. 52 1998 718 727
75. Millington, E. Ph.D. Thesis, Leeds University, 2003.
76. A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, and A. Tijani J. Am. Chem. Soc. 116 1994 4062 4066
77. H.A. Dondas, C.W.G. Fishwick, R. Grigg, and C. Kilner Tetrahedron 60 2004 3473 3485
78. R. Grigg, J. Montgomery, and A. Somasunderam Tetrahedron 48 1992 10431 10442