Tandem Nazarov cyclization-halovinylation of divinyl ketones under Vilsmeier conditions: Synthesis of highly substituted cyclopentadienes

Chemical Communications

Volumn 46, Issue 13, 2010, Pages 2247-2249

  Wang, Mang ^a   Han, Feng ^a   Yuan, Hongjuan ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; KETONE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYCLOADDITION; ELIMINATION REACTION; HALOVINYLATION; NAZAROW CYCLIZATION; SYNTHESIS;

EID: 77949589120     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b917703e     Document Type: Article

References (48)

1. Metallocenes, ed., A. Togni, and, R. L. Halterman, Wiley-VCH, New York, 1998
2. R. L. Halterman Chem. Rev. 1992 92 965
3. E. Winterfeldt Chem. Rev. 1993 93 827
4. M. Enders R. W. Baker Curr. Org. Chem. 2006 10 937
5. For selected recent examples of cyclopentadiene synthesis, see: Z. Xi Q. Song J. Chen H. Guan P. Li Angew. Chem., Int. Ed. 2001 40 1913
6. S. Datta A. Odedra R.-S. Liu J. Am. Chem. Soc. 2005 127 11606
7. W. Zhang S. Luo F. Fang Q. Chen H. Hu X. Jia H. Zhai J. Am. Chem. Soc. 2005 127 18
8. J. H. Lee F. D. Toste Angew. Chem., Int. Ed. 2007 46 912
9. H. Funami H. Kusama N. Iwasawa Angew. Chem., Int. Ed. 2007 46 909
10. Y. Kuninobu Y. Nishina T. Matsuki K. Takai J. Am. Chem. Soc. 2008 130 14062
11. R. Breslow J. W. Canary J. Am. Chem. Soc. 1991 113 3950
12. K. Ogawa S. Minegishi K. Komatsu T. Kitagawa J. Org. Chem. 2008 73 5248
13. For reviews on Nazarov rections, see: H. Pellissier Tetrahedron 2005 61 6479
14. A. J. Frontier C. Collison Tetrahedron 2005 61 7577
15. M. A. Tius Eur. J. Org. Chem. 2005 2193
16. For recent examples of Nazarov reactions, see: F. Dhoro M. A. Tius J. Am. Chem. Soc. 2005 127 12472
17. S. Giese, Jr. R. D. Mazzola C. M. Amann A. M. Arif F. G. West Angew. Chem., Int. Ed. 2005 44 6546
18. G. Liang Y. Xu I. B. Seiple D. Trauner J. Am. Chem. Soc. 2006 128 11022
19. W. He J. Huang X. Sun A. J. Frontier J. Am. Chem. Soc. 2007 129 498
20. D. Song A. Rostami F. G. West J. Am. Chem. Soc. 2007 129 12019
21. G. Liang D. Trauner J. Am. Chem. Soc. 2004 126 9544
22. J. Huang A. J. Frontier J. Am. Chem. Soc. 2007 129 8060
23. M. Rueping W. Ieawsuwan A. P. Antonchick B. J. Nachtsheim Angew. Chem., Int. Ed. 2007 46 2097
24. F. Dhoro T. E. Kristensen V. Stockmann G. P. A. Yap M. A. Tius J. Am. Chem. Soc. 2007 129 7256
25. N. Ghavtadze R. Frohlich E.-U. Würthwein Eur. J. Org. Chem. 2008 3656
26. A. P. Marcus A. S. Lee R. L. Davis D. J. Tantillo R. Sarpong Angew. Chem., Int. Ed. 2008 47 6379
27. W. He J. Huang X. Sun A. J. Frontier J. Am. Chem. Soc. 2008 130 300
28. C. J. Rieder K. J. Winberg F. G. West J. Am. Chem. Soc. 2009 131 7504
29. X. Bi D. Dong Q. Liu W. Pan L. Zhao B. Li J. Am. Chem. Soc. 2005 127 4578
30. J. Tan X. Xu L. Zhang Y. Li Q. Liu Angew. Chem., Int. Ed. 2009 48 2868
31. Y. Ma M. Wang D. Li B. Bekturhun J. Liu Q. Liu J. Org. Chem. 2009 74 3116
32. Z. Fu M. Wang Y. Dong J. Liu Q. Liu J. Org. Chem. 2009 74 6105
33. Y. Liu D. Dong Q. Liu Y. Qi Z. Wang Org. Biomol. Chem. 2004 2 28
34. Y.-L. Zhao Q. Liu J.-P. Zhang Z.-Q. Liu J. Org. Chem. 2005 70 6913
35. L. Chen Y. Zhao Q. Liu C. Piao J. Org. Chem. 2007 72 9259
36. J. Liu D. Liang M. Wang Q. Liu Synthesis 2008 3633
37. O. Meth-Cohn and S. P. Stanforth, in Comprehensive Organic Synthesis, ed., C. H. Heathcock, Pergamon Press, New York, 1991, vol. 2, p. 777
38. C. M. Marson Tetrahedron 1992 48 3659
39. M. A. Ogliaruso M. G. Romanelli E. I. Becker Chem. Rev. 1965 65 261
40. Compound 2a can be considered as a potential cyclopentadienone, for a discussion of the properties and reactivity of cyclopentadienones, see: C. Chen C. Xi Y. Jiang X. Hong J. Am. Chem. Soc. 2005 127 8024
41. P. A. Wender T. J. Paxton T. J. Williams J. Am. Chem. Soc. 2006 128 14814
42. 2Et or CONHAr under Vilsmeier conditions were found to afford δ-lactones and δ-lactams, respectively. See: J. Liu M. Wang F. Han Y. Liu Q. Liu J. Org. Chem. 2009 74 5090
43. 2 = 0.1416 (I > 2σ(I))
44. 3 (2.5 equiv) in DMF at ambient conditions for 1.5 h. For experimental details, see ESI.
45. A. Lilienkampf M. P. Johansson K. Wahala Org. Lett. 2003 5 3387
46. For details, please see ESI. As a comparison, no reaction was found when 1a (1.0 mmol) was treated with either concentrated HCl (3.0 equiv) or dry HCl gas (bubbled into the reaction mixture) in 5.0 mL of DMF at 90 °C for 3.0 h. These results provided further support for the proposed mechanism in Scheme 3 For selected recent examples, see: J. Hudon T. A. Cernak J. A. Ashenhurst J. L. Gleason Angew. Chem., Int. Ed. 2008 47 8885
47. J. N. Payette H. Yamamoto J. Am. Chem. Soc. 2007 129 9536
48. J.-K. Liu Chem. Rev. 2006 106 2209