Progress in palladium-catalyzed Diels-Alder [4+2] cycloaddition reaction

Chinese Journal of Organic Chemistry

Volumn 30, Issue 3, 2010, Pages 368-380

  Duan, Zebin ^a   Long, Yuhua ^a   Yang, Dingqiao ^a  

^a SOUTH CHINA NORMAL UNIVERSITY   (China)

Author keywords

4+2 cycloaddition; Diels Alder reaction; Palladium catalyzed; Reaction mechanism; Research progress

Indexed keywords

EID: 77953551543     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (60)

1. For excellent recent reviews on the Diels-Alder reaction, see: (a) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289.
2. (b) Corey, E. J.; Guzman, P. A. Angew. Chem. 1998, 110, 402.
3. (c) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650.
4. (d) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668.
5. (e) Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078.
6. Oikawa, H.; Tokiwano, T. Nat. Prod. Rep. 2004, 21, 321.
7. Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078.
8. For recent reviews about Lewis acids, see: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
9. (b) Desimoni, G.; Faita, G.; Quadrelli, P. Chem. Rev. 2003, 103, 3119.
10. (c) Gennari, C.; Piarulli, U. Chem. Rev. 2003, 103, 3071.
11. (d) McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
12. (e) Diéguez, M.; Pàmies, O.; Claver, C. Chem. Rev. 2004, 104, 3189.
13. (f) Berthod, M.; Mignani, G.; Woodward, G.; Lemaire, M. Chem. Rev. 2005, 105, 1801.
14. (g) Desimoni, G.; Faita, G.; Jorgensen, K. A. Chem. Rev. 2006, 106, 3561.
15. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232.
16. Kuwano, R.; Shige, T. J. Am. Chem. Soc. 2007, 129, 3802.
17. Wang, C.; Tunge, J. A. J. Am. Chem. Soc. 2008, 130, 8118.
18. Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047.
19. Nakano, H.; Suzuki, Y.; Kabuto, C.; Fujita, R.; Hongo, H. J. Org. Chem. 2002, 67, 5011.
20. Lee, P. H.; Lee, K. Angew. Chem., Int. Ed. 2005, 44, 3253.
21. Sgarbossa, P.; Pizzo, E.; Scarso, A.; Sbovata, S. M.; Michelin, R. A.; Mozzon, M.; Strukul, G.; Benetollo, F. J. Organomet. Chem. 2006, 691, 3659.
22. The electrophilicity of p-methoxybenzylidene malononitriles (-10.8) is less than that of a ∂-allyl palladium complex (-10.1): (a) Kuhn, O.; Mayr, H. Angew. Chem., Int. Ed. 1999, 38, 343.
23. (b) Lemek, T.; Mayr, H. J. Org. Chem. 2003, 68, 6880.
24. Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152.
25. Oi, S.; Kashiwag, K.; Lnone, Y. Tetrahedron Lett. 1998, 39, 6253.
26. Murakami, M.; Minamida, R.; Itami, K.; Sawamura, M.; Ito, Y. Chem. Commun. 2000, 2293.
27. Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067.
28. Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2002, 13, 1841.
29. Nakano, H.; Okuyama, Y.; Suzuki, Y.; Fujita, R.; Kabuto, C. Chem. Commun. 2002, 1146.
30. Mancheño, O. G.; Arrayás, R. G.; Carretero, J. C. Organometallics 2005, 24, 557.
31. Sibi, M. P.; Stanley, L. M.; Nie, X.-P.; Venkatraman, L.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 2007, 129, 395.
32. For recent reviews on the hetero-Diels-Alder reactions, see: (a) Buonora, P.; Olsen, J. C.; Oh, T. Tetrahedron 2001, 57, 6099.
33. (b) Jorgensen, K. Angew. Chem., Int. Ed. 2000, 39, 3558.
34. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed., Blackwell, Oxford, UK, 2000, p. 1.
35. Mu, X.-J.; Xia, Z.-N.; Wang, C.-Y.; Panunzio, M.; Zeng, L.-N. Chin. J. Org. Chem. 2009, 29, 61 (in Chinese).
36. Han, B.; Li, J.-L.; Ma, C.; Zhang, S.-J.; Chen, Y.-C. Angew. Chem., Int. Ed. 2008, 47, 9971.
37. Gentili, J.; Barret, R. Tetrahedron Lett. 2005, 46, 1639.
38. Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660.
39. Hercouet, A.; Berrée, F.; Lin, C. H.; Toupet, L.; Carboni, B. Org. Lett. 2007, 9, 1717.
40. Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970.
41. Weibel, D.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1217.
42. Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Org. Chem. Soc. 1997, 119, 11313.
43. Gevorgyan, V.; Takeda, A.; Homma, M.; Sadayori, N.; Radhakrishnan, U.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 727, 6391.
44. Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779.
45. Hashimoto, K.; Komeshima, N.; Koga, K. J. Chem. Soc., Chem. Commun. 1979, 437.
46. Lam, Y. H.; Cheong, P. H. Y.; Mata, J. M. B.; Stanway, S. J.; Gouvemeur, V.; Houk, K. N. J. Am. Chem. Soc. 2009, 757, 1947.
47. Sarkar, N.; Banerjee, A.; Nelson, S. G. J. Am. Chem. Soc. 2008, 130, 9222.
48. Mathieu, B.; Fays, L.; Ghosez, L. Tetrahedron Lett. 2000, 47, 9561.
49. Crosignani, S.; Desimoni, G.; Faita, G.; Filippone, S.; Mortoni, A.; Righetti, P. P.; Zema, M. Tetrahedron Lett. 1999, 40, 7007.
50. Ishihara, K.; Inanaga, K.; Kondo, S.; Funahashi, M.; Yamamoto, H. Synlett 1998, 1053.
51. Crosignani, S.; Desimoni, G.; Faita, G.; Righetti, P. P. Tetrahedron 1998, 54, 15721.
52. (a) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
53. (b) Futatsugi, K.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 1484.
54. Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 51, 845.
55. Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728.
56. Mihara, J.; Hamada, T.; Irie, R.; Katsuki, T. Synlett 1999, 1160.
57. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 750, 3645.
58. Li, L.-S.; Wu, Y.; Hu, Y.-J.; Xia, L.-J.; Wu, Y.-L. Tetrahedron: Asymmetry 1998, 9, 2271.
59. Nishida, A.; Yamanaka, M.; Nakagawa, M. Tetrahedron Lett. 1999, 40, 1555.
60. Shi, L.; Yu, S.-W.; Liao, S.-J.; Yu, D.-R.; Shen, Q.; Hong, F.; Yu, S.-Z. Acta Chim. Sinica 1995, 53, 1010 (in Chinese).