Synthesis of anti-2,7-disubstituted norbornadienes

Synthesis

Volumn , Issue 4, 2009, Pages 609-619

  Tsui, Gavin C ^a   Marquand, Paul Le ^a   Allen, Anna ^a   Tam, William ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Bicyclic compounds; Catalysis; Cross coupling; Iron; Palladium

Indexed keywords

ALKYL GROUPS; ALKYNYL GROUPS; BICYCLIC COMPOUNDS; CATALYZED COUPLINGS; COUPLING PRODUCTS; CROSS-COUPLING; CROSS-COUPLING REACTIONS; EFFICIENT SYNTHESIS; RING SIZES; TRIFLATE;

CATALYSIS; PALLADIUM; SUGAR (SUCROSE);

COMPLEXATION;

ALKYL GROUP; ALKYNYL GROUP; IRON; NORBORNADIENE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CROSS COUPLING REACTION; SYNTHESIS;

EID: 63849318204     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083352     Document Type: Article

References (82)

1. (a) Julius Hyman & Co.; Belgian Patent; 498, 176, 1951.
2. (b) Lautens, M.; Tam, W. Advances in Metal-Organic Chemistry, Vol. 6; JAI Press: New York, 1998, 49.
3. Houk, K. N.; Domelsmith, L. N.; Mollerer, P. D.; Hahn, R. C.; Johnson, R. P. J. Am. Chem. Soc. 1978, 100, 2959.
4. Khoury, P. R.; Goddard, J. D.; Tam, W. Tetrahedron 2004, 60, 8103.
5. Corey, E. J.; Shibasaki, M.; Nicolaou, K. C.; Malmsten, C. L.; Samuelsson, B. Tetrahedron Lett. 1976, 17, 737.
6. Lee, M.; Ikeda, I.; Kawabe, T.; Mori, S.; Kanematsu, K. J. Org. Chem. 1996, 61, 3406.
7. (a) Sato, K.; Miyamoto, O.; Inoue, S.; Honda, K. Chem. Lett. 1981, 10, 1183.
8. (b) Monti, H.; Corriol, C.; Bertrand, M. Tetrahedron Lett. 1982, 23, 5539.
9. (a) Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508.
10. (b) Shintani, R.; Ueyama, K.; Yamada, I.; Hayashi, T. Org. Lett. 2004, 6, 3425.
11. (c) Shintani, R.; Okamoto, K.; Otomaru, Y.; Ueyama, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 54.
12. For reviews, see: (a) Bren, V. A.; Dubonosov, A. D.; Minkin, V. I.; Chernoivanov, V. A. Russ. Chem. Rev. 1991, 60, 913.
13. (b) Dubonosov, A. D.; Bren, V. A.; Chernoivanov, V. A. Russ. Chem. Rev. 2002, 71, 917.
14. (a) Hirao, K.; Ando, A.; Hamada, T.; Yonemitsu, O. J. Chem. Soc., Chem. Commun. 1984, 300.
15. (b) Bonfantini, E. E.; Officer, D. L. J. Chem. Soc., Chem. Commun. 1994, 1445.
16. (c) Maafi, M.; Lion, C.; Aaron, J. J. New J. Chem. 1996, 20, 559.
17. (d) Franceschi, F.; Guardigli, M.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Inorg. Chem. 1997, 36, 4099.
18. (e) Ikeda, A.; Tsubata, A.; Kameyama, A.; Nishikubo, T. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 917.
19. (a) Nishikubo, T.; Shimokawa, T.; Sahara, A. Macromolecules 1989, 22, 8.
20. (b) Kinoshita, K.; Horie, K.; Morino, S.; Nishikudo, T. Appl. Phys. Lett. 1997, 70, 2940.
21. (c) Takahashi, S.; Samata, K.; Mura, H.; Machida, S.; Horie, K. Appl. Phys. Lett. 2001, 78, 13.
22. Kato, Y.; Muta, H.; Takahashi, S.; Horie, K.; Nagai, T. Polym. J. 2001, 33, 868.
23. Winkler, T.; Dix, I.; Jones, P. G.; Herges, R. Angew. Chem. Int. Ed. 2003, 42, 3541.
24. For synthesis of 7-substituted norbornadienes 2, see:
25. (a) Story, P. R.; Fahrenholtz, S. R. J. Org. Chem. 1963, 28, 1716.
26. (b) Clarke, S. C.; Johnson, B. L. Tetrahedron 1968, 24, 5067.
27. (c) Story, P. R.; Fahrenholtz, S. R. Org. Synth. 1973, 151.
28. (d) Baxter, A. D.; Binus, F.; Javed, T.; Roberts, S. M.; Dalder, P.; Scheinmann, F.; Wakefield, B. J.; Lynch, M.; Newton, R. F. J. Chem. Soc., Perkin Trans. 1 1986, 5067.
29. For synthesis of 2-substituted and 2,3-disubstituted norbornadienes by Diels-Alder reactions between cyclopentadiene and an alkyne, see:
30. (a) Trost, B. M.; Fleming, I.; Paquette, L. A. In Comprehensive Organic Synthesis, Vol. 5; Pergamon: Oxford, 1991, Chap. 4.1.
31. (b) Ishihara, K.; Kondo, S.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 3026; and references cited therein.
32. (c) Corey, E. J.; Lee, T. W. Tetrahedron Lett. 1997, 38, 5755; and references cited therein.
33. For synthesis of 2-substituted and 2,3-disubstituted norbornadienes by deprotonation of norbornadiene, see
34. (a) Stäble, M.; Lehmann, R.; Kramař, J.; Schlosser, M. Chimia 1985, 39, 229.
35. (b) Verkruijsse, H. D.; Brandsma, L. Recl. Trav. Chim. Pays-Bas 1986, 105, 66.
36. (c) Kenndoff, J.; Polborn, K.; Szeimies, G. J. Am. Chem. Soc. 1990, 112, 6117.
37. (d) Tranmer, G. K.; Yip, C.; Handerson, S.; Jordan, R. W.; Tam, W. Can. J. Chem. 2000, 78, 527.
38. Tranmer, G. K.; Tam, W. Synthesis 2002, 1675.
39. Yoo, W.-J.; Tsui, G. C.; Tam, W. Eur. J. Org. Chem. 2005, 1044.
40. (a) Ciganek, E. Org. React. 1984, 32, 1.
41. (b) The Diels-Alder Reaction; Fringuelli, F.; Taticchi, A., Eds.; John Wiley & Sons: West Sussex, 2002.
42. Edwards, L. E. Ph.D. Thesis; University of Toronto: Canada, 1992.
43. For reviews of the Shapiro reaction, see (a) Shapiro, R. H. Org. React. 1976, 23, 405.
44. (b) Adlington, R. M.; Barrett, A. G. M. Acc. Chem. Res. 1983, 16, 55.
45. (c) Chamberlin, A. R.; Bloom, S. H. Org. React. 1990, 39, 1.
46. For reviews of the Pd-catalyzed Suzuki coupling reactions,
47. see
48. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
49. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions, Chap. 2; Diederich, F.; Stang, P. J., Eds.; Wiley- VCH, Weinheim: Germany, 1998.
50. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
51. (d) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
52. (e) Miura, M. Angew Chem. Int. Ed. 2004, 43, 2201.
53. For reviews on Sonogashira coupling, see
54. (a) Sonogsahira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: London, 1998, 203.
55. (b) Sonogsahira, K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991, 521.
56. For early work on Fe-catalyzed alkenylations, see:
57. (a) Kharasch, M. S.; Fuchs, C. F. J. Org. Chem. 1945, 10, 292.
58. (b) Kharasch, M. S.; Lambert, F. L.; Urry, W. H. J. Org. Chem. 1945, 10, 298.
59. (c) Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487.
60. (d) Neumann, S. M.; Kochi, J. K. J. Org. Chem. 1975, 40, 599.
61. For selected recent examples of Fe-catalyzed alkenylations, see:
62. (a) Molander, G. A.; Rahn, B. J.; Shubert, D. C.; Bonde, S. E. Tetrahedron Lett. 1983, 24, 5449.
63. (b) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199.
64. (c) Bogdanovic, B.; Schwickardi, M. Angew. Chem. Int. Ed. 2000, 39, 4610.
65. (d) Dohle, W.; Kopp, F.; Cahiez, G.; Knochel, P. Synlett 2001, 1901.
66. (e) Fürstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
67. (f) Scheiper, B.; Bonnekessel, M.; Krause, H.; Furstner, A. J. Org. Chem. 2004, 69, 3943.
68. (g) Martin, R.; Furstner, A. Angew. Chem. Int. Ed. 2004, 43, 3955.
69. (h) Furstner, A.; Martin, R. Chem. Lett. 2005, 34, 624.
70. (i) Ottesen, L. K.; Ek, F.; Olsson, R. Org. Lett. 2006, 8, 1771.
71. (j) Xu, X.; Cheng, D.; Pei, W. J. Org. Chem. 2006, 71, 6637.
72. (k) Furstner, A.; Krause, H.; Lehmann, C. W. Angew. Chem. Int. Ed. 2006, 45, 440.
73. (l) Cahiez, G.; Habiak, V.; Duplais, C.; Moyeux, A. Angew. Chem. Int. Ed. 2007, 46, 4364.
74. (m) Guerinot, A.; Reymond, S.; Cossy, J. Angew. Chem. Int. Ed. 2007, 46, 6521.
75. (n) Chowdhury, R. R.; Crane, A. K.; Fowler, C.; Kwong, P.; Kozak, C. M. Chem. Commun. 2008, 94.
76. (o) Fürstner, A.; Majima, K.; Martin, R.; Krause, H.; Kattnig, E.; Goddard, R.; Lehmann, C. W. J. Am. Chem. Soc. 2008, 130, 1992.
77. Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2003, 42, 308.
78. Fürstner, A.; De Souza, D.; Parra-Rapado, L.; Jensen, J. Angew. Chem. Int. Ed. 2003, 42, 5358.
79. Seidel, G.; Laurich, D.; Furstner, A. J. Org. Chem. 2004, 69, 3950.
80. Neumann, S. M.; Kochi, J. K. J. Org. Chem. 1975, 40, 599.
81. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
82. Krasovskiy, A.; Knochel, P. Synthesis 2006, 890.