Michael addition reaction of alkenyl triehloroacetates catalyzed by dibutyltin dimethoxide

Chemistry Letters

Volumn 37, Issue 10, 2008, Pages 1092-1093

  Yanagisawa, Akira ^a   Izumi, Youhei ^a   Arai, Takayoshi ^a  

^a CHIBA UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 67650476659     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2008.1092     Document Type: Article

References (27)

1. For recent examples of Michael addition of enolates, see: a) S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2582.
2. b) K. Miura, T. Nakagawa, A. Hosomi, Synlett 2003, 2068.
3. c) K. Miura, T. Nakagawa, A. Hosomi, Synlett 2005, 1917.
4. d) T. Nakagawa, H. Fujisawa, Y. Nagata, T. Mukaiyama, Bull. Chem. Soc. Jpn. 2005, 78, 236.
5. e) T. Tozawa, Y. Yamane, T. Mukaiyama, Chem. Lett. 2006, 35, 56.
6. f) T. Tozawa, Y. Yamane, T. Mukaiyama, Chem. Lett. 2006, 35, 360.
7. g) T. Mukaiyama, H. Nagao, Y. Yamane, Chem. Lett. 2006, 35, 916.
8. h) M. Agostinho, S. Kobayashi, J. Am. Chem. Soc. 2008, 130, 2430.
9. i) S. Kobayashi, T. Tsubogo, S. Saito, Y. Yamashita, Org. Lett. 2008, 10, 807.
10. j) A. Takahashi, H. Yanai, T. Taguchi, Chem. Commun. 2008, 2385.
11. For representative reviews, see: a) C. H. Heathcock, in Comprehensive Organic Synthesis, ed. by B. M. Trost, I. Fleming, C. H. Heathcock, Pergamon, Oxford, 1991, Vol. 2, p. 133.
12. b) M. E. Jung, in Comprehensive Organic Synthesis, ed. by B. M. Trost, I. Fleming, M. F. Semmelhack, Pergamon, Oxford, 1991, Vol. 4, p. 1.
13. a) X. Wang, S. Adachi, H. Iwai, H. Takatsuki, K. Fujita, M. Kubo, A. Oku, T. Harada, J. Org. Chem. 2003, 68, 10046.
14. b) D. Liu, S. Hong, E. J. Corey, J. Am. Chem. Soc. 2006, 128, 8160.
15. c) N. Takenaka, J. P. Abell, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 742.
16. d) H. Yang, S. Kim, Synlett 2008, 555.
17. A. Yanagisawa, T. Sekiguchi, Tetrahedron Lett. 2003, 44, 7163.
18. For Michael addition reactions of organotin enolates, see: a) I. Shibata, Y. Mori, H. Yamasaki, A. Baba, H. Matsuda, Tetrahedron Lett. 1993, 34, 6567.
19. b) I. Shibata, M. Nishio, A. Baba, H. Matsuda, J. Chem. Soc, Chem. Commun. 1993, 1067.
20. c) I. Shibata, K. Yasuda, Y. Tanaka, M. Yasuda, A. Baba, J. Org. Chem. 1998, 63, 1334.
21. d) M. Yasuda, N. Ohigashi, I. Shibata, A. Baba, J. Org. Chem. 1999, 64, 2180.
22. e) M. Yasuda, Y. Matsukawa, K. Okamoto, T. Sako, N. Kitahara, A. Baba, Chem. Commun. 2000, 2149.
23. f) M. Yasuda, N. Ohigashi, A. Baba, Chem. Lett. 2000, 1266.
24. g) M. Yasuda, K. Chiba, N. Ohigashi, Y. Katoh, A. Baba, J. Am. Chem. Soc. 2003, 125, 7291.
25. h) M. Yasuda, Y. Shigeyoshi, I. Shibata, A. Baba, Synthesis 2005, 233.
26. In the absence of MeOH, the reaction did not occur catalytically.
27. 4 and concentrated in vacuo after filtration. The residual crude product was purified by column chromatography on silica gel to give the benzoquinone derivative 3.