Facile one-pot construction of polycyclic frameworks using a synergistic diels-alder reaction, ene reaction, and allylation reaction strategy

Chemistry - An Asian Journal

Volumn 6, Issue 2, 2011, Pages 392-395

  Li, Dongzhen ^a   Cao, Yang ^a   Shi, An ^a   Xi, Zhenfeng ^a,b  

^a PEKING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

allylation; Diels Alder reactions; ene reaction; polycycles; synergistic strategy

Indexed keywords

ALLYLATIONS; DIELS-ALDER REACTION; ENE REACTION; POLYCYCLES; SYNERGISTIC STRATEGY;

CHEMICAL REACTIONS;

ALLYL COMPOUND; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; METHODOLOGY; SYNTHESIS;

ALLYL COMPOUNDS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS;

EID: 79251519648     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000257     Document Type: Article

References (60)

1. For recent reviews on domino/cascade reactions, see
2. J. Barluenga, F. Rodriguez, F. J. Fananas, Chem. Asian J. 2009, 4, 1036
3. L. F. Tietze, T. Kinzel, C. C. Brazel, Acc. Chem. Soc. 2009, 42, 367
4. L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis; Wiley-VCH, Weinheim, 2006
5. K. C. Nicolaou, E. W. Yue, T. Oshima, in The New Chemistry (Ed.:, N. Hall,), Cambridge University Press, Cambridge, 2001, p. 168; see also
6. B. Jiang, S.-J. Tu, P. Kaur, W. Wever, G. Li, J. Am. Chem. Soc. 2009, 131, 11660
7. K. J. Frankowski, J. E. Golden, Y. Zeng, Y. Lei, J. Aube, J. Am. Chem. Soc. 2008, 130, 6018
8. E. Jiménez-Núñez, C. K. Claverie, C. Nieto-Oberhuber, A. M. Echavarren, Angew. Chem. 2006, 118, 5578
9. Angew. Chem. Int. Ed. 2006, 45, 5452
10. E. Jiménez-Núñez, M. Raducan, T. Lauterbach, K. Molawi, C. R. Solorio, A. M. Echavarren, Angew. Chem. 2009, 121, 6268
11. Angew. Chem. Int. Ed. 2009, 48, 6152
12. N. Shindoh, Y. Takemoto, K. Takasu, Chem. Eur. J. 2009, 15, 7026
13. L. F. Tietze, A. Dufert, F. Lotz, L. Solter, K. Oum, T. Lenzer, T. Beck, R. Herbst-Irmer, J. Am. Chem. Soc. 2009, 131, 17879
14. H. W. Sünnemann, M. G. Banwell, A. De Meijere, Chem. Eur. J. 2008, 14, 7236
15. A. Yanagisawa, T. Arai, Chem. Commun. 2008, 1165
16. K. Zheng, J. Shi, X. H. Liu, X. M. Feng, J. Am. Chem. Soc. 2008, 130, 15770.
17. For recent reviews on multi-component syntheses, see
18. B. Touré, D. G. Hall, Chem. Rev. 2009, 109, 4439
19. Multicomponent Reactions (Eds.:, J. Zhu, H. Bienayme,), Wiley-VCH, Weinheim, Germany, 2005
20. A. Jacobi von Wangelin, H. Neumann, D. Gordes, S. Klaus, D. Strubing, M. Beller, Chem. Eur. J. 2003, 9, 4286
21. G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101
22. J. Zhu, Eur. J. Org. Chem. 2003, 1133. see also
23. A. Dömling, Chem. Rev. 2006, 106, 17
24. D. M. D'Souza, T. J. J. Muller, Chem. Soc. Rev. 2007, 36, 1095
25. Y. Yamamoto, H. Hayashi, Tetrahedron 2007, 63, 10149
26. D. Strübing, A. Kirschner, H. Neumann, S. Klaus, U. T. Bornscheuer, M. Beller, Chem. Eur. J. 2005, 11, 4210.
27. For atom economy, see
28. B. M. Trost, G. Dong, Nature 2008, 456, 485
29. B. M. Trost, Acc. Chem. Res. 2002, 35, 695
30. B. M. Trost, Science 1991, 254, 1471.
31. For step economy, see
32. M. P. Croatt, P. A. Wender, Eur. J. Org. Chem. 2010, 19
33. P. A. Wender, J. L. Baryza, S. E. Brenner, M. O. Clarke, G. G. Gamber, J. C. Horan, T. C. Jessop, C. Kan, K. Pattabiraman, T. J. Williams, Pure Appl. Chem. 2003, 75, 143
34. P. A. Wender, F. C. Bi, G. G. Gamber, F. Gosselin, R. D. Hubbard, M. J. C. Scanio, R. Sun, T. J. Williams, L. Zhang, Pure Appl. Chem. 2002, 74, 25; see also
35. I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193.
36. W.-X. Zhang, Z. Xi, Synlett 2008, 2557; and references therein.
37. For a recent review, see
38. M. E. Welker, Tetrahedron 2008, 64, 11529; see also
39. D. Li, G. Liu, Q. Hu, C. Wang, Z. Xi, Org. Lett. 2007, 9, 5433
40. D. Li, A. Shi, W.-X. Zhang, G. Liu, Z. Xi, Tetrahedron 2008, 64, 9895
41. M. Shimizu, K. Shimono, T. Kurahashi, S. I. Kiyomoto, I. Nagao, T. Hayashi, Bull. Chem. Soc. Jpn. 2008, 81, 518
42. D. J. Zhang, J. G. Xin, Y. L. Liu, X. Zhou, X. H. Liu, X. M. Feng, J. Org. Chem. 2008, 73, 630.
43. For the use of 1,3-butadiene as an ene reaction component, see
44. M. L. Clarke, M. B. France, Tetrahedron 2008, 64, 9003
45. S. Yao, M. Johannsen, K. A. Jørgensen, J. Chem. Soc. Perkin Trans. 1 1997, 2345
46. C. Qian, T. Huang, Tetrahedron Lett. 1997, 38, 6721
47. E. Hayashi, Y. Takahashi, H. Itoh, N. Yoneda, Bull. Chem. Soc. Jpn. 1994, 67, 3040
48. B. B. Snider, E. Ron, J. Am. Chem. Soc. 1985, 107, 8160
49. H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597
50. Angew. Chem. Int. Ed. Engl. 1969, 8, 556.
51. For some recent examples on intramolecular allylation using allylsilanes, see
52. J. T. Spletstoser, M. J. Zacuto, J. L. Leighton, Org. Lett. 2008, 10, 5593
53. J. Beignet, P. J. Jervis, L. R. Cox, J. Org. Chem. 2008, 73, 5462
54. R. Shintani, Y. Ichikawa, T. Hayashi, J. Chen, Y. Nakao, T. Hiyama, Org. Lett. 2007, 9, 4643
55. F. Peng, D. G. Hall, J. Am. Chem. Soc. 2007, 129, 3070
56. P. J. Jervis, B. M. Kariuki, L. R. Cox, Org. Lett. 2006, 8, 4649
57. H. Yamamoto, M. Wadamoto, J. Am. Chem. Soc. 2005, 127, 14556
58. X. Wang, Q. Meng, N. R. Perl, Y. Xu, J. L. Leighton, J. Am. Chem. Soc. 2005, 127, 12806
59. L. Chabaud, P. James, Y. Landais, Eur. J. Org. Chem. 2004, 3173.
60. CCDC 749964 (3b), CCDC 749962 (6), and CCDC 749963 (8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via