Trapping the oxyallyl cation intermediate derived from the Nazarov cyclization of allenyl vinyl ketones with nitrogen heterocycles

Advanced Synthesis and Catalysis

Volumn 353, Issue 1, 2011, Pages 64-68

  Marx, Vanessa M ^a   Lefort, François M ^a   Burnell, D Jean ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

allenes; cyclization; heterocycles; interrupted reaction; Nazarov reaction

Indexed keywords

EID: 79251479095     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000722     Document Type: Article

References (38)

1. For reviews on the Nazarov reaction, see: K. L. Habermas, S. E. Denmark, T. K. Jones, Org. React. 1994, 45, 1-158
2. H. Pellissier, Tetrahedron 2005, 61, 6479-6517
3. A. J. Frontier, C. Collison, Tetrahedron 2005, 61, 7577-7606
4. M. A. Tius, Eur. J. Org. Chem. 2005, 2193-2206
5. W. Nakanishi, F. G. West., Curr. Opin. Drug Discovery Dev. 2009, 12, 732-751.
6. For some recent examples of the development of Nazarov reaction methodology and applications in synthesis, see: C. J. Rieder, K. J. Winberg, F. G. West, J. Am. Chem. Soc. 2009, 131, 7504-7505
7. J. A. Malona, K. Cariou, A. J. Frontier, J. Am. Chem. Soc. 2009, 131, 7560-7561
8. R. Singh, M. K. Parai, G. Panda, Org. Biomol. Chem. 2009, 7, 1858-1867
9. A. Y. Bitar, A. J. Frontier, Org. Lett. 2009, 11, 49-52
10. N. Shimada, B. O. Ashburn, A. K. Basak, W. F. Bow, D. A. Vicic, M. A. Tius, Chem. Commun. 2010, 46, 3774-3775
11. M. Wang, F. Han, H. Yuan, Q. Liu., Chem. Commun. 2010, 46, 2247-2249
12. M. Kawatsura, K. Kajita, S. Hayase, T. Itoh, Synlett 2010, 1243-1246
13. P. A. Wender, R. T. Stemmler, L. E. Sirois, J. Am. Chem. Soc. 2010, 132, 2532-2533
14. T. Vaidya, A. C. Atesin, I. R. Herrick, A. J. Frontier, R. Eisenberg, Angew. Chem. Int. Ed. 2010, 49, 3363-3366
15. W. F. Bow, A. K. Basak, A. Jolit, D. A. Vicic, M. A. Tius, Org. Lett. 2010, 12, 440-443
16. F. Churruca, M. Fousteris, Y. Ishikawa, M. von Wantoch Rekowski, C. Hounsou, T. Surrey, A. Giannis, Org. Lett. 2010, 12, 2096-2099
17. K. E. Lazarski, D. X. Hu, C. L. Stern, R. J. Thomson, Org. Lett. 2010, 12, 3010-3013
18. P. Cao, C. Deng, Y.-Y. Zhou, X.-L. Sun, J.-C. Zheng, Z. Xie, Y. Tang, Angew. Chem. Int. Ed. 2010, 49, 4463-4466
19. A. K. Basak, N. Shimada, W. F. Bow, D. A. Vicic, M. A. Tius, J. Am. Chem. Soc. 2010, 132, 8266-8267
20. A. Srikrishna, G. Neetu, Tetrahedron: Asymmetry 2010, 21, 2067-2071.
21. M. A. Tius, C.-K. Kwok, X. Gu, C. Zhao, Synth. Commun. 1994, 24, 871-885
22. A. S. K. Hashmi, J. W. Bats, J.-H. Choi, L. Schwarz, Tetrahedron Lett. 1998, 39, 7491-7494
23. M. A. Tius, Acc. Chem. Res. 2003, 36, 284-290, and references cited therein
24. P. Cao, X.-L. Sun, B.-H. Zhu, Q. Shen, Z. Xie, Y. Tang, Org. Lett. 2009, 11, 3048-3051.
25. For a review on the interrupted Nazarov reaction, see:, T. N. Grant, C. J. Rieder, F. G. West, Chem. Commun. 2009, 5676-5688.
26. V. M. Marx, D. J. Burnell, Org. Lett. 2009, 11, 1229-1231.
27. V. M. Marx, T. S. Cameron, D. J. Burnell, Tetrahedron Lett. 2009, 50, 7213-7216.
28. V. M. Marx, D. J. Burnell, J. Am. Chem. Soc. 2010, 132, 1685-1689.
29. C. J. Rieder, R. J. Fradette, F. G. West, Chem. Commun. 2008, 1572-1574
30. C. J. Rieder, R. J. Fradette, F. G. West, Heterocycles 2010, 1413-1427.
31. Furan had been observed to undergo [4+3] cycloadditions with oxyallyl cations: M. Harmata, P. Rashatasakhon, Tetrahedron 2003, 59, 2371-2395, and references cited therein
32. Y. Wang, B. D. Schill, A. M. Arif, F. G. West, Org. Lett. 2003, 5, 2747-2750.
33. A. K. Basak, M. A. Tius, Org. Lett. 2008, 10, 4073-4076.
34. Under the same reaction conditions but in the presence of thiophene, no identifiable Nazarov product was obtained.
35. The trans stereochemistry was confirmed by NOE measurements and the magnitudes of coupling constants.
36. 1H NMR spectrum of the crude reaction mixture.
37. 1H NMR spectroscopy of the crude product mixtures that 1 was reacting mainly by Michael reactions with the pyrroles.
38. Observation of NOE's established the Z-geometry of 17.