Cadmium promoted allylation of acid chlorides: Synthesis of β,γ-unsaturated ketones

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9087-9088

  Baruah, Bipul ^a   Boruah, Anima ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CADMIUM; KETONE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; METHODOLOGY;

EID: 0030577460     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02092-8     Document Type: Article

References (23)

1. 1 Noyce, D. S., Evett, M., J. Org. Chem., 1972,57,394, 397; Aumiller, J. C., Whittle, J. A., J. Org. Chem. 1976, 41,2959.
2. 1 Noyce, D. S., Evett, M., J. Org. Chem., 1972,57,394, 397; Aumiller, J. C., Whittle, J. A., J. Org. Chem. 1976, 41,2959.
3. 2 Ringold, H. J., Malhotra, S. K., Tetrahedron Lett., 1962, 669; Sandheimer, F., Mazur, Y., J. Am. Chem. Soc., 1957,79,2906; Paquette, L. A., Elzember, R. F., J. Am. Chem. Soc., 1967, 89, 6205; Padwa, A., Crumrine, D., Hartman, R., Layton, R., J. Am. Chem. Soc., 1967, 89, 4435.
4. 2 Ringold, H. J., Malhotra, S. K., Tetrahedron Lett., 1962, 669; Sandheimer, F., Mazur, Y., J. Am. Chem. Soc., 1957,79,2906; Paquette, L. A., Elzember, R. F., J. Am. Chem. Soc., 1967, 89, 6205; Padwa, A., Crumrine, D., Hartman, R., Layton, R., J. Am. Chem. Soc., 1967, 89, 4435.
5. 2 Ringold, H. J., Malhotra, S. K., Tetrahedron Lett., 1962, 669; Sandheimer, F., Mazur, Y., J. Am. Chem. Soc., 1957,79,2906; Paquette, L. A., Elzember, R. F., J. Am. Chem. Soc., 1967, 89, 6205; Padwa, A., Crumrine, D., Hartman, R., Layton, R., J. Am. Chem. Soc., 1967, 89, 4435.
6. 2 Ringold, H. J., Malhotra, S. K., Tetrahedron Lett., 1962, 669; Sandheimer, F., Mazur, Y., J. Am. Chem. Soc., 1957,79,2906; Paquette, L. A., Elzember, R. F., J. Am. Chem. Soc., 1967, 89, 6205; Padwa, A., Crumrine, D., Hartman, R., Layton, R., J. Am. Chem. Soc., 1967, 89, 4435.
7. 3 Beak, P., Berger, K. R., J. Am. Chem. Soc., 1980, 102, 3848; Hoffman, H. M. R., Tsushima, T., J. Am. Chem. Soc., 1977, 99, 6008.
8. 3 Beak, P., Berger, K. R., J. Am. Chem. Soc., 1980, 102, 3848; Hoffman, H. M. R., Tsushima, T., J. Am. Chem. Soc., 1977, 99, 6008.
9. 4 Onaka, M., Goto, T., Mukaiyama, T., Chem. Lett., 1979, 1483.
10. 5 Zaidlewicz, M., Synthesis, 1988, 701.
11. 6 Hosomi, A., Hashimoto, H., Sakurai, H., J. Org. Chem., 1978, 43, 2551; Laguerre, M., Dunogues, J., Calas, R., Tetrahedron Lett., 1980, 21, 831; Hayashi, T., Konishi, M., Ito, H., Kumuda, M., J. Am. Chem. Soc., 1982, 104, 4962.
12. 6 Hosomi, A., Hashimoto, H., Sakurai, H., J. Org. Chem., 1978, 43, 2551; Laguerre, M., Dunogues, J., Calas, R., Tetrahedron Lett., 1980, 21, 831; Hayashi, T., Konishi, M., Ito, H., Kumuda, M., J. Am. Chem. Soc., 1982, 104, 4962.
13. 6 Hosomi, A., Hashimoto, H., Sakurai, H., J. Org. Chem., 1978, 43, 2551; Laguerre, M., Dunogues, J., Calas, R., Tetrahedron Lett., 1980, 21, 831; Hayashi, T., Konishi, M., Ito, H., Kumuda, M., J. Am. Chem. Soc., 1982, 104, 4962.
14. 7 Sato, T., Kawara, T., Nishizawa, A., Fujisawa, T., Tetrahedron Lett., 1980, 21,3377.
15. 8 Hegedus, I. S., Kendall, P. M., Lo, S. M., Sheats, J. R., J. Am. Chem. Soc., 1975, 97, 5448.
16. 9 Cahiez, G., Laboue, B., Tetrahedron Lett., 1989, 30, 7369.
17. 10 Kasatkin, A. N., Kulak, A. N., Tolstikov, G. A., J. Organomet. Chem., 1988, 346, 23.
18. 11 Larock, R. C., Lu, Y., J. Org. Chem., 1993, 58, 2846.
19. 12 Tiecco, M., Testaferri, L., Tingoli, M., Bagnoli, L., Santi, C., Syn. Lett., 1993, 798.
20. 13 For a most recent multistep report see: Brown, H. C., Soundararajan, R., Tetrahedron Lett., 1994, 35, 6963.
21. 14 Cadmium powder used was of commercial grade and procured from Central Drug House (Pvt.) Ltd., New Delhi-110002.
22. 15 Acid chlorides either were obtained commercially or prepared according to known procedures and distilled before use.
23. 16 Curran, D. P., Kim, B. H., Synthesis, 1986, 312.