Synthesis of 1,4-Diketones: Unusual Coupling of Tin Enolates with α-Chloro Ketones Catalyzed by Zinc Halides

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8282-8283

  Yasuda, Makoto ^a   Tsuji, Shoki ^a   Shibata, Ikuya ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001087233     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971624z     Document Type: Article

References (45)

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30. The five-coordinate tin enolate is derived from the four-coordinate tin enolate and an appropriate ligand. (a) Baba, A.; Yasuda, M.; Yano, K.; Shibata, I.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (b) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans, 1 1993, 859-865. Yasuda, M.; Katoh, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. Yasuda, M.; Morimoto, J.; Shibata, I.; Baba, A. Tetrahedron Lett. 1997, 38, 3265-3266.
31. The five-coordinate tin enolate is derived from the four-coordinate tin enolate and an appropriate ligand. (a) Baba, A.; Yasuda, M.; Yano, K.; Shibata, I.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (b) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans, 1 1993, 859-865. Yasuda, M.; Katoh, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. Yasuda, M.; Morimoto, J.; Shibata, I.; Baba, A. Tetrahedron Lett. 1997, 38, 3265-3266.
32. The five-coordinate tin enolate is derived from the four-coordinate tin enolate and an appropriate ligand. (a) Baba, A.; Yasuda, M.; Yano, K.; Shibata, I.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (b) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans, 1 1993, 859-865. Yasuda, M.; Katoh, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. Yasuda, M.; Morimoto, J.; Shibata, I.; Baba, A. Tetrahedron Lett. 1997, 38, 3265-3266.
33. The five-coordinate tin enolate is derived from the four-coordinate tin enolate and an appropriate ligand. (a) Baba, A.; Yasuda, M.; Yano, K.; Shibata, I.; Matsuda, H. J. Chem. Soc., Perkin Trans. 1 1990, 3205-3207. (b) Yasuda, M.; Oh-hata, T.; Shibata, I.; Baba, A.; Matsuda, H. J. Chem. Soc., Perkin Trans, 1 1993, 859-865. Yasuda, M.; Katoh, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386-4392. Yasuda, M.; Morimoto, J.; Shibata, I.; Baba, A. Tetrahedron Lett. 1997, 38, 3265-3266.
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35. For reviews, see: (a) Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 85-100. (b) Yasuda, M.; Shibata, I.; Baba, A.; Matsuda, H. Recent Res. Dev. Pure Appl. Chem. 1997, 1, 55-71.
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43. Organotin enolates exist as equilibrium mixtures of keto and/ or enol forms; 1b and 1d exclusively exist in keto and enol forms, respectively, and 1a and 1c is a mixture of both forms. Pereyre, M; Bellegarde, B; Mendelsohn, J; Valade, J. J. Organomet. Chem. 1968, 11, 97-110.
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