Ring-closing metathesis on solid support: Elaboration of a cyclization/cleavage strategy towards unsaturated α-ester-substituted N-heterocycles

European Journal of Organic Chemistry

Volumn , Issue 11, 1998, Pages 2583-2589

  Veerman, J J N ^a   Van Maarseveen, Jan H ^b   Visser, Geb M ^b   Kruse, Chris G ^b   Schoemaker, Hans E ^a   Hiemstra, Henk ^a   Rutjes, Floris P J T ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b Solvay Pharmaceuticals Inc   (Netherlands)

Author keywords

Amino acids; Cyclization cleavage; N Heterocycles; Ring closing metathesis; Solid phase

Indexed keywords

EID: 2842617271     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199811)1998:11<2583::AID-EJOC2583>3.0.CO;2-G     Document Type: Article

References (77)

1. [1a] Special issue on combinatorial chemistry: Acc. Chem. Res. 1996, 29 (3).
2. [1b] M. A. Gallop, R. W. Barrett, W. J. Dower, S. P. A. Fodor, E. M. Gordon, J. Med. Chem. 1994, 37, 1233.
3. [1c] E. M. Gordon, R. W. Barrett, W. J. Dower, S. P. A. Fodor, M. A. Gallop, J. Med. Chem. 1994, 37, 1386.
4. [2a] P. H. H. Hermkens, H. C. J. Ottenheijm, D. Rees, Tetrahedron 1996, 52, 4527.
5. [2b] P. H. H. Hermkens. H. C. J. Ottenheijm, D. Rees, Tetrahedron 1997, 53, 5643.
6. [3a] F. Balkenhohl, C. Von dem Bussche-Hünnefeld, A. Lansky, Zechel, C., Angew. Chem. Int. Ed. Engl. 1996, 35, 2288.
7. [3b] L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555.
8. [3c] J. S. Früchtel, G. Jung, Angew Chem. Int. Ed. Engl 1996, 35, 17.
9. [3d] N. K. Terrett, M. Gardner, D. W. Gordon, R. S. Kobylecki, J. Steele, Tetrahedron 1995, 51, 8135.
10. [3e] A. Nefzi, J. M. Ostresh, R. A. Houghten, Chem. Rev. 1997, 97, 449.
11. [4a] M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1995, 60, 6006.
12. [4b] B. C. Chenera, J. A. Finkelstein, D. F. Veber, J. Am. Chem. Soc. 1995, 117, 11999.
13. [4c] F. X. Woolard, J. Paetsch, J. A. Ellman, J. Org. Chem. 1997, 62, 6102.
14. [4d] M. J. Plunkett, Ellman, J. A,. J Org. Chem 1997, 62, 2885.
15. [4e] Y. Han, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 270.
16. [4f] T. L. Boehm, H. D. H. Showalter, J. Org. Chem. 1996, 61, 6498.
17. [5a] A L. Smith, C. G Thomson, P. D. Leeson, Bioorg. Med. Chem. Lett 1996, 6, 1483 and references cited therein.
18. [5b] J. Kowalski, M. A. Lipton, Tetrahedron Lett. 1996, 37, 5839.
19. [5c] B. A. Dressman, L. A. Spangle, S. W. Kaldor, Tetrahedron Lett. 1996, 37, 937.
20. [6d] R. H. Grubbs, S. Chang. Tetrahedron 1998, 54, 4413.
21. [6d] R. H. Grubbs, S. Chang. Tetrahedron 1998, 54, 4413.
22. [6d] R. H. Grubbs, S. Chang. Tetrahedron 1998, 54, 4413.
23. [6d] R. H. Grubbs, S. Chang. Tetrahedron 1998, 54, 4413.
24. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
25. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
26. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
27. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
28. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
29. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
30. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
31. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
32. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
33. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
34. [7k] A. K. Ghosh, K. A. Hussain, Tetrahedron Lett. 1998, 59, 1881.
35. [8g] D. J. O'Leary, S. J. Miller, R. H. Grubbs, Tetrahedron Lett. 1998, 39, 1689.
36. [8g] D. J. O'Leary, S. J. Miller, R. H. Grubbs, Tetrahedron Lett. 1998, 39, 1689.
37. [8g] D. J. O'Leary, S. J. Miller, R. H. Grubbs, Tetrahedron Lett. 1998, 39, 1689.
38. [8g] D. J. O'Leary, S. J. Miller, R. H. Grubbs, Tetrahedron Lett. 1998, 39, 1689.
39. [8g] D. J. O'Leary, S. J. Miller, R. H. Grubbs, Tetrahedron Lett. 1998, 39, 1689.
40. [8g] D. J. O'Leary, S. J. Miller, R. H. Grubbs, Tetrahedron Lett. 1998, 39, 1689.
41. [8g] D. J. O'Leary, S. J. Miller, R. H. Grubbs, Tetrahedron Lett. 1998, 39, 1689.
42. J. H. Van Maarseveen, J. A. J. Den Hartog, V. Engelen, E. Finner, G. Visser, C. G. Kruse, Tetrahedron Lett. 1996, 37, 8249.
43. F. P. J. T. Rutjes, H. E. Schoemaker, Tetrahedron Lett. 1997, 38, 677.
44. K. C Nicolaou, N. Winssinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hamel, Nature 1997, 387, 268.
45. [12a] A. D. Piscopio, J. F. Miller, K. Koch, Tetrahedron Lett. 1997, 38, 7143.
46. [12b] A. D. Piscopio J. F. Miller, K. Koch, Tetrahedron Lett. 1998, 39, 2667.
47. [13a] J.-U. Peters, S. Blechert, Synlett 1997, 348.
48. [13b] M. Schuster, J. Pernerstorfer, S. Blechert, Angew. Chem Int. Ed. Engl. 1996, 35, 1979.
49. [13c] J. Pernerstorfer, M. Schuster, S. Blechert, J. Chem Soc., Chem. Commun. 1997, 1949.
50. S. Marquais, M. Arlt, Tetrahedron Lett. 1996, 37, 5491.
51. O. Mitsunobu, Synthesis, 1981, 1.
52. B. F. Gisin, Helv. Chim. Acta. 1973, 56, 1476.
53. B Yan, G. Kumaravel, Tetrahedron 1996, 52, 843.
54. M. Schwarz, J. E. Oliver, P. E. Sonnet, J. Org. Chem. 1975, 40, 2410.
55. This sequence was repeated on a Wang-resin, followed by TFA-mediated cleavage and full characterization of the residue to confirm the yield of the bromination reaction.
56. [20d] M. J. O'Donnell, R. L. Polt, J. Org. Chem. 1982, 47, 2663.
57. [20d] M. J. O'Donnell, R. L. Polt, J. Org. Chem. 1982, 47, 2663.
58. [20d] M. J. O'Donnell, R. L. Polt, J. Org. Chem. 1982, 47, 2663.
59. [20d] M. J. O'Donnell, R. L. Polt, J. Org. Chem. 1982, 47, 2663.
60. [22] Reaction of styrene with 5 mol% of Ru catalyst in toluene for 17 h at 50°C resulted in the formation of 2% of stilbene (determined by GC analysis).
61. For a general mechanistic study of RCM, see: E. L. Dias, S. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1997, 119, 3887.
62. C. Sylvain, A. Wagner, C. Mioskowski, Tetrahedron Lett. 1997, 38, 1043.
63. [25a] L. F. Tietze, A. Steinmetz, Angew. Chem. Int. Ed. Engl. 1996, 35, 651.
64. [25b] D. R. Tortolani, S. A. Biller, Tetrahedron Lett. 1996, 37, 5687.
65. [25c] R. Frenette, R. W. Friesen, Tetrahedron Lett. 1994, 35, 9177.
66. L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041.
67. [27a] M. Mergler, R. Nijfeler, J. Gosteli, Tetrahedron Lett. 1989, 30, 6741.
68. [27b] K. Ngu, D.V. Patel, Tetrahedron Lett. 1997, 38, 973.
69. T. Fukuyama, C.-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373
70. [29a] X. Beebe, N. E. Schore M. J. Kurth, J. Am. Chem. Soc 1992, 114, 10061.
71. [29b] X. Beebe, N. E. Schore, M. J. Kurth, J. Org. Chem. 1995, 60, 4196.
72. [29c] J. M. Frechet, C. Schuerch, J. Am. Chem Soc 1971, 93, 492.
73. E. W. Colvin, R. A. Raphael, J. S. Roberts, J. Chem. Soc., Chem. Commun. 1971, 858.
74. [31a] D. P. Rotella, J Am. Chem. Soc. 1996, 118. 12246.
75. [31b] C. Chen, Ahlberg L. A. Randall, R. B. Miller, A. D. Jones, M. J. Kurth. J. Am. Chem. Soc. 1994, 116, 2661.
76. [31c] C. C. Leznoff. J. Y. Wong, Can. J. Chem. 1973, 51, 3756.
77. D. B. Bryan, R. F. Hall, K. G. Holden, W. F. Huffman, J. G. Gleason, J. Am Chem. Soc. 1977, 99, 2353.