A convenient synthesis of β,γ-unsaturated ketones through zinc-mediated allylation of acid chlorides

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 1109-1112

  Ranu, Brindaban C ^a   Majee, Adinath ^a   Das, Asish R ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030070673     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02317-8     Document Type: Article

References (27)

1. Demuth, M.; Mikhail, G. Synthesis 1989, 145.
2. (a). Groves, J. K. Chem. Soc. Rev. 1972, 1, 73.
3. (b). Noyce, D. S.; Evett, M. J.Org.Chem. 1972, 37, 394, 397.
4. (c). Aumiller, J. C.; Whittle, J. A. J. Org. Chem. 1976, 41, 2959.
5. (a). Monti, S. A.; White, G.L. J. Org. Chem. 1975, 40, 215.
6. (b). Hoffman, H. M. R.; Tsushima, T. J. Am. Chem. Soc. 1977, 99, 6008.
7. (c). Beak, P.; Berger, K. R. J. Am. Chem. Soc. 1980, 102, 3848.
8. (d). Earnshaw, C.; Torr, R. S.; Warren, S. S. J. Chem. Soc. Perkin Trans. 1 1983, 2893.
9. Onaka, M.; Goto, T.; Mukaiyama, T. Chem. Lett. 1979, 1483.
10. Kachinsky, J. L C.; Salomon, R. G. J. Org. Chem. 1986, 51, 1393.
11. Zaidlewicz, M. Synthesis 1988, 701.
12. Brown, H. C.; Soundararajan, R. Tetrahedron Lett. 1994, 35, 6963.
13. (a). Hosomi, A.; Hashimoto, H.; Sakurai, H. J. Org. Chem. 1978, 43, 2551.
14. (b). Laguerre, M.; Dunogues, J.; Calas, R. Tetrahedron Lett. 1980, 21, 831.
15. (c). Hayashi, T.; Konishi, M.; Ito, H.; Kumuda, M. J. Am. Chem. Soc. 1982, 104, 4962.
16. Labadie, J. W.; Tueting, D.; Stille, J. K. J. Org. Chem. 1983, 48, 4634.
17. Sato, T.; Kawara, T.; Nishizawa, A.; Fujisawa, T. Tetrahedron Lett. 1980, 21, 3377.
18. Hegedus, I. S.; Kendall, P. M.; Lo, S. M.; Sheats, J. R. J. Am. Chem. Soc. 1975, 97, 5448.
19. Cahiez, G.; Laboue, B. Tetrahedron Lett. 1989, 30, 7369.
20. Kasatkin, A. N.; Kulak, A. N.; Tolstikov, G. A. J. Organomet. Chem. 1988, 346, 23.
21. Larock, R. C.; Lu, Y. J. Org. Chem. 1993, 58, 2846.
22. Ranu, B. C.; Majee, A.; Das, A. R. Tetrahedron Lett. 1995, 36, 4885.
23. Without sonication the reaction is very sluggish.
24. The progress of the reaction was monitored by TLC to avoid any chance of further addition to produce alcohols.
25. Usually, the preparation of allylzinc derivatives is reported to require activated zinc to initiate the reaction: Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.
26. (a). Shchepin, V. V.; Russkikh, N. Yu.; Novoselova, E. V.; Lapkins, 1.1.; Gartman, G. A. Zh. Org. Khim. 1987, 23, 506.
27. (b) Auvray, P.; Knochel, P.; Normant, J. F. Tetrahedron 1988, 44, 4495.