Preparation of Enaminones by Two-Carbon Homologation of Amides with Lithium (Triphenylsilyl)acetylide

Journal of Organic Chemistry

Volumn 52, Issue 13, 1987, Pages 2929-2930

  Suzuki, Keisuke ^a   Ohkuma, Takeshi ^a   Tsuchihashi, Gen ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0842311914     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00389a052     Document Type: Article

References (8)

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3. Leonard, N. J.; Adamcik, J. A. J. Am. Chem. Soc. 1959,81, 595. (b) Meyers, A. I.; Singh, S. Tetrahedron Lett. 1967, 5319. (c) Meyers, A. I.; Reine, A. H.; Gault, R.; J. Org. Chem. 1969, 34, 698. (d) Yoshimoto, M.; Ishida, N.; Hiraoka, T. Tetrahedron Lett. 1973, 39. (e) Abdulla, R. F.; Fuhr, K. H. J. Org. Chem. 1978,43,4248. (f) Mukaiyama, T.; Ohsumi, T. Chem. Lett. 1983. 875.
4. Baraldi, P. G.; Simoni, D.; Manfredini, S. Synthesis 1983, 902. (b) Gupton, J.; Andrew, S.; Cohen, C. Synth. Commun. 1982,12, 35. (c) Bowden, K.; Braude, E. A.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 45. (d) Mestres, R. J. Chem. Soc., Perkin Trans. 1 1972, 805. (e) Murahashi, S. I. ; Tsumiyama, T.; Yo, M. Chem. Lett. 1984,1419. (f) Kashima, C.; Aoyama, H.; Yamamoto, Y.; Nishio, T. J. Chem. Soc., Perkin Trans. 2 1975, 665. (g) Hasek, R. H.; Martin, J. C. J. Org. Chem. 1963, 28, 1468. (h) Bozell, J. J.; Hegedus, L. S. J. Org. Chem. 1981, 46, 2561. (i) Matsuyama, Y.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983,105, 6312. (j) Pohland, A. E.; Benson, W. R. Chem. Rev. 1966, 66, 161 and references cited therein.
5. Suzuki, K.; Ohkuma, T.; Miyazawa, M.; Tsuchihashi, G. Tetrahedron Lett. 1986, 27, 373.
6. Reaction of Me3Si- or t-BuMe2Si-acetylide gave the corresponding alkynone 4, while Ph2MeSi-acetylide gave a varying mixture of 4 and 5 depending on the conditions. For the related examples of Me3Si cases, see: Cupps, T. L.; Boutin, R. H.; Rapoport, H. J. Org, Chem. 1985, 50, 3972.
7. For related ring expansion of lactones, see: Schreiber, S. L.; Kelly, S. E. Tetrahedron Lett. 1984, 25, 1757.
8. Yamaguchi, M.; Waseda, T.; Hirao, I. Chem. Lett. 1983, 35.