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http://dx.doi.org/10.5012/bkcs.2010.31.03.670

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  

Lee, Young-Un (Department of Chemistry and Institute for Natural Sciences, Hanyang University)
Lim, Choong-Min (Department of Chemistry and Institute for Natural Sciences, Hanyang University)
Kim, Sung-Hwan (Department of Chemistry, Kyungpook National University)
Shin, Seung-Hoon (Department of Chemistry and Institute for Natural Sciences, Hanyang University)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.3, 2010 , pp. 670-677 More about this Journal
Abstract
A comparative study on the Au(I)-catalyzed and IBr-promoted tandem cyclization of 1,5-enyne was reported. This study provides a meaningful mechanistic insight to the concerted nature of this tandem reaction and also provides interesting applications in the synthesis of 7/5- or 8/5-fused bicycles and biaryls.
Keywords
Gold catalysis; Iodocyclization; Tandem reaction; 1,5-Enyne; Carbocycles;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 3  (Related Records In Web of Science)
Times Cited By SCOPUS : 4
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1 Tietze, L. F. Chem. Rev. 1996, 96, 115.   DOI   ScienceOn
2 Malacria, M. Chem. Rev. 1996, 96, 289.   DOI   ScienceOn
3 Burke, M. D.; Schreiber, S. L. Angew. Chem. Int. Ed. 2004, 43, 46.   DOI   ScienceOn
4 Jimenez-Nunez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326.   DOI   ScienceOn
5 Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.   DOI   ScienceOn
6 Michelet, V.; Toullec, P. Y.; Genêt, J. P. Angew. Chem. Int. Ed. 2008, 47, 4268.   DOI   ScienceOn
7 Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.   DOI   ScienceOn
8 Furstner, A.; Davies, P. W. Angew. Chem. Int. Ed. 2007, 46, 3410.   DOI   ScienceOn
9 Lim, C.; Kang, J.-E.; Lee, J.-E.; Shin, S. Org. Lett. 2007, 9, 3539.   DOI   ScienceOn
10 Kang, J.-E.; Lee, E. S.; Park, S. I.; Shin, S. Tetrahedron Lett. 2005, 46, 7431.   DOI   ScienceOn
11 Kang, J.-E.; Shin, S. Synlett 2006, 717.
12 Buzas, A.; Gagosz, F. Synlett 2006, 2727.
13 Lee, E.-S.; Yeom, H.-S.; Hwang, J.-H.; Shin, S. Eur. J. Org. Chem. 2007, 3503.
14 Buzas, A.; Istrate, F. M.; Gagosz, F. Tetrahedron 2009, 65, 1889.   DOI   ScienceOn
15 Cheong, J. Y.; Bae, H. J.; Baskar, B.; Thangadurai, D.; Kim, M.-J.; Rhee, Y. H. Bull. Korean Chem. Soc. 2009, 30, 1239.   DOI   ScienceOn
16 Lim, C.; Rao, M. S.; Shin, S. Synlett in press
17 Yamamoto, Y.; Gridnev, I. D.; Patil, N. T.; Jin, T. Chem. Commun. 2009, 5075.
18 Duan, J. J.-W.; Smith, A. B. J. Org. Chem. 1993, 58, 3703.   DOI   ScienceOn
19 Trost, B. M.; Machacek, M. R.; Tsui, H. C. J. Am. Chem. Soc. 2005, 127, 7014.   DOI   ScienceOn
20 Smith, A. B.; Kim, D.-S.; Xian, M. Org. Lett. 2007, 9, 3307.   DOI   ScienceOn
21 Trost, B. M.; Chan, D. M. T.; Nanninga, T. N. Org. Synth. 1984, 62, 58.   DOI
22 Okazaki, T.; Laali, K. K. J. Org. Chem. 2005, 70, 9139.   DOI   ScienceOn
23 Okazaki, T.; Laali, K. K. J. Org. Chem. 2006, 71, 9643.   DOI   ScienceOn
24 Strozier, R. W.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1979, 79, 1340.
25 Hayashi, T. Acc. Chem. Res. 2000, 33, 354.   DOI   ScienceOn
26 Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681.   DOI   ScienceOn
27 Istrate, F.; Buzas, A.; Dias Jurberg, I.; Odabachian, Y.; Gagosz, F. Org. Lett. 2008, 10, 925.   DOI   ScienceOn
28 Hayashi, T. J. Organomet. Chem. 1999, 576, 195.   DOI   ScienceOn
29 Uozumi, Y.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1993, 4, 2419.   DOI   ScienceOn
30 Hashmi, A. S. K.; Salathe, R.; Frey, W. Synlett 2007, 1763.
31 Buzas, A.; Istrate, F.; Le Goff, X. F.; Odabachian, Y.; Gagosz, F. J. Organomet. Chem. 2009, 694, 515.   DOI   ScienceOn