An Acylative C-C Single-Bond Cleavage and a Self-Cyclization of Ethyl 2-(Trimethylsilylmethyl)penta-2,4-dienoate or Its Free Acid under Ritter Condition

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 5, 1996, Pages 1409-1416

  Kuroda, Chiaki ^a   Mitsumata, Naoko ^a   Tang, Chen Ying ^a  

^a RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000094230     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1409     Document Type: Article

References (29)

1. G. Majetich, "Organic Synthesis: Theory and Application," ed by T. Hudlicky, JAI Press, Greenwich (1989), Vol. 1, p. 173; B. M. Trost, Angew. Chem., Int. Ed. Engl., 25, 1 (1986); G. L. Larson, "The Chemistry of Organic Silicon Compounds," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1989), p. 763; E. Langkopf and D. Schinzer, Chem. Rev., 95, 1375 (1995).
2. G. Majetich, "Organic Synthesis: Theory and Application," ed by T. Hudlicky, JAI Press, Greenwich (1989), Vol. 1, p. 173; B. M. Trost, Angew. Chem., Int. Ed. Engl., 25, 1 (1986); G. L. Larson, "The Chemistry of Organic Silicon Compounds," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1989), p. 763; E. Langkopf and D. Schinzer, Chem. Rev., 95, 1375 (1995).
3. G. Majetich, "Organic Synthesis: Theory and Application," ed by T. Hudlicky, JAI Press, Greenwich (1989), Vol. 1, p. 173; B. M. Trost, Angew. Chem., Int. Ed. Engl., 25, 1 (1986); G. L. Larson, "The Chemistry of Organic Silicon Compounds," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1989), p. 763; E. Langkopf and D. Schinzer, Chem. Rev., 95, 1375 (1995).
4. G. Majetich, "Organic Synthesis: Theory and Application," ed by T. Hudlicky, JAI Press, Greenwich (1989), Vol. 1, p. 173; B. M. Trost, Angew. Chem., Int. Ed. Engl., 25, 1 (1986); G. L. Larson, "The Chemistry of Organic Silicon Compounds," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1989), p. 763; E. Langkopf and D. Schinzer, Chem. Rev., 95, 1375 (1995).
5. C. Kuroda, S.Shimizu, and J. Y. Satoh, J. Chem. Soc., Chem. Commun., 1987, 286; J. Chem. Soc., Perkin Trans, 1, 1990, 519; C. Kuroda, S. Inoue, S. Kato, and J. Y. Satoh, J. Chem. Res. (S), 1993, 62; C. Kuroda, S. Inoue, R. Takemura, and J. Y. Satoh, J. Chem. Soc., Perkin Trans. 1, 1994, 521; C. Kuroda and K. Ito, J. Chem. Res. (S), 1995, 270.
6. C. Kuroda, S.Shimizu, and J. Y. Satoh, J. Chem. Soc., Chem. Commun., 1987, 286; J. Chem. Soc., Perkin Trans, 1, 1990, 519; C. Kuroda, S. Inoue, S. Kato, and J. Y. Satoh, J. Chem. Res. (S), 1993, 62; C. Kuroda, S. Inoue, R. Takemura, and J. Y. Satoh, J. Chem. Soc., Perkin Trans. 1, 1994, 521; C. Kuroda and K. Ito, J. Chem. Res. (S), 1995, 270.
7. C. Kuroda, S.Shimizu, and J. Y. Satoh, J. Chem. Soc., Chem. Commun., 1987, 286; J. Chem. Soc., Perkin Trans, 1, 1990, 519; C. Kuroda, S. Inoue, S. Kato, and J. Y. Satoh, J. Chem. Res. (S), 1993, 62; C. Kuroda, S. Inoue, R. Takemura, and J. Y. Satoh, J. Chem. Soc., Perkin Trans. 1, 1994, 521; C. Kuroda and K. Ito, J. Chem. Res. (S), 1995, 270.
8. C. Kuroda, S.Shimizu, and J. Y. Satoh, J. Chem. Soc., Chem. Commun., 1987, 286; J. Chem. Soc., Perkin Trans, 1, 1990, 519; C. Kuroda, S. Inoue, S. Kato, and J. Y. Satoh, J. Chem. Res. (S), 1993, 62; C. Kuroda, S. Inoue, R. Takemura, and J. Y. Satoh, J. Chem. Soc., Perkin Trans. 1, 1994, 521; C. Kuroda and K. Ito, J. Chem. Res. (S), 1995, 270.
9. C. Kuroda, S.Shimizu, and J. Y. Satoh, J. Chem. Soc., Chem. Commun., 1987, 286; J. Chem. Soc., Perkin Trans, 1, 1990, 519; C. Kuroda, S. Inoue, S. Kato, and J. Y. Satoh, J. Chem. Res. (S), 1993, 62; C. Kuroda, S. Inoue, R. Takemura, and J. Y. Satoh, J. Chem. Soc., Perkin Trans. 1, 1994, 521; C. Kuroda and K. Ito, J. Chem. Res. (S), 1995, 270.
10. K. Nishitani and K. Yamakawa reported similar reaction shortly after our publication: Tetrahedron Lett., 28, 655 (1987); K. Nishitani, Y. Nakamura, R. Orii, C. Arai, and K. Yamakawa, Chem. Pharm. Bull, 41, 822 (1993).
11. K. Nishitani and K. Yamakawa reported similar reaction shortly after our publication: Tetrahedron Lett., 28, 655 (1987); K. Nishitani, Y. Nakamura, R. Orii, C. Arai, and K. Yamakawa, Chem. Pharm. Bull, 41, 822 (1993).
12. C. Kuroda, Y. Ohnishi, and J. Y. Satoh, Tetrahedron Lett., 34, 2613 (1993).
13. C. Kuroda, S. Shimizu, T. Haishima, and J. Y. Satoh, Bull. Chem. Soc. Jpn., 66, 2298 (1993).
14. C. Kuroda and Y. Hirono, Tetrahedron Lett., 35, 6895 (1994).
15. J, Pornet, B. Khouz, and L. Miginiac, Tetrahedron Lett., 26, 1861 (1985); J. Pornet, A. Rayadh, and L. Miginiac, Tetrahedron Lett., 27, 5479 (1986).
16. J, Pornet, B. Khouz, and L. Miginiac, Tetrahedron Lett., 26, 1861 (1985); J. Pornet, A. Rayadh, and L. Miginiac, Tetrahedron Lett., 27, 5479 (1986).
17. Preliminary communications: C. Kuroda and N. Mitsumata, Chem. Lett., 1994, 1375.
18. For Ritter reaction, see: R. Bishop, "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 6, p. 261.
19. a) T. Fujiwara, K. Monta, and T. Takeda, Bull. Chem. Soc. Jpn., 62, 1524 (1989);
20. b) W. M. Best and D. A. Widdowson, Tetrahedron, 45, 5943 (1989).
21. R. M. Adlington and A. G. M. Barrett, J. Chem. Soc., Perkin Trans, 1. 1981, 2848.
22. G. P. Boldrini, D. Savoia, E. Tagliavini, C. Trombini, and A. Umani-Ronchi, J. Org. Chem., 48, 4108 (1983).
23. M. A. Brook, C. Henry, R. Jueschke, and P. Modi, Synlett, 1993, 97.
24. L. S. Hegedus, S. D. Wagner, E. L. Waterman, and K. Siirala-Hansen, J. Org. Chem., 40, 593 (1975).
25. J. M. Cassady and M. Suffness, "Anticancer Agents Based on Natural Product Models," ed by J. M. Cassady and J. D. Douros, Academic Press, New York (1980), p. 201.
26. For Review, see: P. A. Grieco, Synthesis, 1975, 67; R. B. Gammill, C. A. Wilson, and T. A. Bryson, Synth. Commun., 5, 245 (1975). For recent examples, see: T. Minami, K. Hirakawa, S. Koyanagi, S. Nakamura, and M. Yamaguchi, J. Chem. Soc., Perkin Trans. 1, 1990, 2385; Y. Rollin, S. Derien, E. Dunach, C. Gebehenne, and J. Perichon, Tetrahedron, 49, 7723 (1993); see also Refs. 2 and 3.
27. For Review, see: P. A. Grieco, Synthesis, 1975, 67; R. B. Gammill, C. A. Wilson, and T. A. Bryson, Synth. Commun., 5, 245 (1975). For recent examples, see: T. Minami, K. Hirakawa, S. Koyanagi, S. Nakamura, and M. Yamaguchi, J. Chem. Soc., Perkin Trans. 1, 1990, 2385; Y. Rollin, S. Derien, E. Dunach, C. Gebehenne, and J. Perichon, Tetrahedron, 49, 7723 (1993); see also Refs. 2 and 3.
28. For Review, see: P. A. Grieco, Synthesis, 1975, 67; R. B. Gammill, C. A. Wilson, and T. A. Bryson, Synth. Commun., 5, 245 (1975). For recent examples, see: T. Minami, K. Hirakawa, S. Koyanagi, S. Nakamura, and M. Yamaguchi, J. Chem. Soc., Perkin Trans. 1, 1990, 2385; Y. Rollin, S. Derien, E. Dunach, C. Gebehenne, and J. Perichon, Tetrahedron, 49, 7723 (1993); see also Refs. 2 and 3.
29. For Review, see: P. A. Grieco, Synthesis, 1975, 67; R. B. Gammill, C. A. Wilson, and T. A. Bryson, Synth. Commun., 5, 245 (1975). For recent examples, see: T. Minami, K. Hirakawa, S. Koyanagi, S. Nakamura, and M. Yamaguchi, J. Chem. Soc., Perkin Trans. 1, 1990, 2385; Y. Rollin, S. Derien, E. Dunach, C. Gebehenne, and J. Perichon, Tetrahedron, 49, 7723 (1993); see also Refs. 2 and 3.