Synthesis of cyclohexene derivatives from 1,5-enynes via gold-catalysis and iodocyclization: A comparative study and applications in the synthesis of 7/5- or 8/5-fused rings and biaryls

Bulletin of the Korean Chemical Society

Volumn 31, Issue 3, 2010, Pages 670-677

  Lee, Youngun ^a   Lim, Choongmin ^a   Kim, Sunghwan ^b   Shin, Seunghoon ^a  

^a Hanyang University   (South Korea)

^b Kyungpook National University   (South Korea)

Author keywords

1,5 enyne; Carbocycles; Gold catalysis; Iodocyclization; Tandem reaction

Indexed keywords

BIARYLS; CARBOCYCLES; COMPARATIVE STUDIES; CYCLOHEXENES; FUSED RING; GOLD CATALYSIS; IODOCYCLIZATION; TANDEM CYCLIZATION; TANDEM REACTION;

CATALYSIS; CYCLIZATION; GOLD; OLEFINS;

SYNTHESIS (CHEMICAL);

EID: 77951829384     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.03.670     Document Type: Article

References (31)

1. (a) Tietze, L. F. Chem. Rev. 1996, 96, 115.
2. (b) Malacria, M. Chem. Rev. 1996, 96, 289.
3. (c) Burke, M. D.; Schreiber, S. L. Angew. Chem. Int. Ed. 2004, 43, 46.
4. For recent reviews, see (a) Jiménez-Núnez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326.
5. (b) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
6. (c) Michelet, V.; Toullec, P. Y.; Genêt, J. P. Angew. Chem. Int. Ed. 2008, 47, 4268.
7. (d) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
8. (e) Fürstner, A.; Davies, P. W. Angew. Chem. Int. Ed. 2007, 46, 3410.
9. (a) Lim, C.; Kang, J.-E.; Lee, J.-E.; Shin, S. Org. Lett. 2007, 9, 3539.
10. (b) Kang, J.-E.; Lee, E. S.; Park, S. I.; Shin, S. Tetrahedron Lett. 2005, 46, 7431.
11. (c) Kang, J.-E.; Shin, S. Synlett 2006, 717.
12. (d) Buzas, A.; Gagosz, F. Synlett 2006, 2727.
13. (e) Lee, E.-S.; Yeom, H.-S.; Hwang, J.-H.; Shin, S. Eur. J. Org. Chem. 2007, 3503.
14. (f) Hashmi, A. S. K.; Salathé, R.; Frey, W. Synlett 2007, 1763.
15. (g) Istrate, F.; Buzas, A.; Dias Jurberg, I.; Odabachian, Y.; Gagosz, F. Org. Lett. 2008, 10, 925.
16. (h) Buzas, A.; Istrate, F.; Le Goff, X. F.; Odabachian, Y.; Gagosz, F. J. Organomet. Chem. 2009, 694, 515.
17. (i) Buzas, A.; Istrate, F. M.; Gagosz, F. Tetrahedron 2009, 65, 1889.
18. (j) Cheong, J. Y.; Bae, H. J.; Baskar, B.; Thangadurai, D.; Kim, M.-J.; Rhee, Y. H. Bull. Korean Chem. Soc. 2009, 30, 1239.
19. (a) Lim, C.; Rao, M. S.; Shin, S. Synlett in press (doi #: S11009ST). For a recent review comparing metal-catalyzed and iodoniumtriggered reactions, see:
20. (b) Yamamoto, Y.; Gridnev, I. D.; Patil, N. T.; Jin, T. Chem. Commun. 2009, 5075. For a prototypical iodocarbonatation of olefin, see:
21. (d) Duan, J. J.-W.; Smith, A. B. J. Org. Chem. 1993, 58, 3703.
22. (a) Trost, B. M.; Machacek, M. R.; Tsui, H. C. J. Am. Chem. Soc. 2005, 127, 7014.
23. (b) Smith, A. B.; Kim, D.-S.; Xian, M. Org. Lett. 2007, 9, 3307.
24. (c) Trost, B. M.; Chan, D. M. T.; Nanninga, T. N. Org. Synth. 1984, 62, 58.
25. (a) Okazaki, T.; Laali, K. K. J. Org. Chem. 2005, 70, 9139.
26. (b) Okazaki, T.; Laali, K. K. J. Org. Chem. 2006, 71, 9643.
27. (c) Strozier, R. W.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1979, 79, 1340.
28. (a) Hayashi, T. Acc. Chem. Res. 2000, 33, 354.
29. (b) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681.
30. (c) Hayashi, T. J. Organomet. Chem. 1999, 576, 195.
31. (d) Uozumi, Y.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1993, 4, 2419.