Oxidation-initiated nazarov cyclization of vinyl alkoxyallenes

Organic Letters

Volumn 13, Issue 3, 2011, Pages 414-417

  Spencer III, William T ^a   Levin, Mark D ^a   Frontier, Alison J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLENE; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; CYCLOPENTANES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 79851498246     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1027255     Document Type: Article

References (39)

1. (a) Nazarov, I. N.; Zaretskaya, I. I. Izv. Akad. Nauk. SSSR, Ser. Khim. 1941, 211.
2. (b) Santelli-Rouvier, C.; Santelli, M. Synthesis 1983, 429.
3. (c) Habermas, K. L.; Denmark, S. E.; Jones, T. K. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York, 1994; Vol. 45, pp 1-158.
4. (d) Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577.
5. (e) Pellissier, H. Tetrahedron 2005, 61, 6479.
6. (f) Tius, M. A. Eur. J. Org. Chem. 2005, 11, 2193.
7. (g) Grant, T. N.; Rieder, C. J.; West, F. G. Chem. Commun. 2009, 5676.
8. (h) Nakanishi, W.; West, F. G. Curr. Opin. Drug Disco V. 2009, 12, 732.
9. (a) Iso-Nazarov example: Miller, A. K.; Banghart, M. R.; Beaudry, C. M.; Suh, J. M.; Trauner, D. Tetrahedron 2003, 59, 8919.
10. (b) Aza-Nazarov example: Dieker, J.; Fröhlich, R.; Würthwein, E.-U. Eur. J. Org. Chem. 2006, 23, 5339.
11. (c) Metallo-Nazarov example: Lemiere, G.; Gandon, V.; Cariou, K.; Fukuyama, T.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2007, 9, 2207.
12. (d) Dichlorocyclopropane Nazarov example: Grant, T. N.; West, F. G. J. Am. Chem. Soc. 2006, 128, 9348.
13. (e) Vinylogous Nazarov example: Rieder, C. J.; Winberg, K. J.; West, F. G. J. Am. Chem. Soc. 2009, 131, 7504.
14. (f) Allenyl aryl carbinol Nazarov example: Cordier, P.; Aubert, C.; Malacria, M.; Lacote, E.; Gandon, V. Angew. Chem., Int. Ed. 2009, 48, 8757.
15. Malona, J. A.; Cariou, K.; Frontier, A. J. J. Am. Chem. Soc. 2009, 131, 7560.
16. For an example of Nazarov cyclization triggered by protonation (rather than oxidation) of an allene, see: (a) Wu, Y. K.; West, F. G. J. Org. Chem. 2010, 75, 5410. For an example of a Nazarov cyclization that affords products similar to those described here, see:
17. (b) Basak, A. K.; Shimada, N.; Bow, W. F.; Vicic, D. A.; Tius, M. A. J. Am. Chem. Soc. 2010, 132, 8266.
18. Recent reviews on the lipoxygenase pathway for jasmonate formation: (a) Schaller, A.; Stintzi, A. Phytochemistry 2009, 70, 1532.
19. (b) Gfeller, A.; Dubugnon, L.; Liechti, R.; Farmer, E. E. Sci. Signal. 2010, 3, cm3.
20. (a) Grimaldi, J.; Bertrand, M. Tetrahedron Lett. 1969, 38, 3269.
21. (b) Bertrand, M.; Dulcere, J.-P.; Grimaldi, J. C. R. Seances Acad. Sci., Ser. C 1974, 279, 805.
22. (c) Bertrand, M.; Dulcere, J.-P.; Gil, G.; Roumestant, M. L. Tetrahedron Lett. 1979, 21, 1845.
23. (d) Doutheau, A.; Gore, J.; Malacria, M. Tetrahedron 1977, 33, 2393.
24. (e) Dulcere, J.-P.; Grimaldi, J.; Santelli, M. Tetrahedron Lett. 1981, 22, 3179.
25. (f) Kim, S. J.; Cha, J. K. Tetrahedron Lett. 1988, 29, 5613.
26. For examples of formation of allene diepoxides with DMDO, see: (a) Lotesta, S. D.; Kiren, S.; Sauers, R. R.; Williams, L. J. Angew. Chem., Int. Ed. 2007, 46, 7108.
27. (b) Zhang, Y.; Cusick, J. R.; Ghosh, P.; Shangguan, N.; Katukojvala, S.; Inghrim, J.; Emge, T. J.; Williams, L. J. J. Org. Chem. 2009, 74, 7707.
28. (c) Ghosh, P.; Cusick, J. R.; Inghrim, J.; Williams, L. J. Org. Lett. 2009, 11, 4672.
29. Stereochemistry of Nazarov products was determined by NOE analysis (see the Supporting Information).
30. This stereochemical assignment is based upon past observations, which indicate that bond formation occurs on the least hindered face of the pentadienyl cation: (a) Denmark, S. E.; Habermas, K. L.; Hite, G. A.; Jones, T. K. Tetrahedron 1986, 42, 2821.
31. (b) Denmark, S. E.; Habermas, K. L.; Hite, G. A. Helv. Chim. Acta 1988, 71, 168.
32. (c) Denmark, S. E.; Wallace, M. A.; Walker, C. B., Jr. J. Org. Chem. 1990, 55, 5543.
33. (d) Paquette, L. A.; Kang, H.-J. J. Am. Chem. Soc. 1991, 113, 2610.
34. (e) Occhiato, E. G.; Prandi, C.; Ferrali, A.; Guarna, A.; Venturello, P. J. Org. Chem. 2003, 68, 9728.
35. (f) Prandi, C.; Ferrali, A.; Guarna, A.; Venturello, P.; Occhiato, E. G. J. Org. Chem. 2004, 69, 7705.
36. Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 15, 4319.
37. Crandall, J. K.; Batal, D. J.; Sebesta, D. P.; Lin, F. J. Org. Chem. 1991, 56, 1153.
38. Sandrinelli, F.; Perrio, S.; Beslin, P. J. Org. Chem. 1997, 62, 8626.
39. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. 1969, 8, 781.