Zirconium-catalyzed carboalumination of alkynes and enynes as a route to aluminacycles and their conversion to cyclic organic compounds

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2503-2506

  Negishi, Ei Ichi ^a   Montchamp, Jean Luc ^a   Anastasia, Luigi ^a   Elizarov, Arkadij ^a   Choueiry, Danièle ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CYCLOPENTENE DERIVATIVE; ORGANIC COMPOUND; ZIRCONIUM;

ARTICLE; CATALYSIS; CHEMICAL BINDING; DRUG SYNTHESIS; MOLECULAR INTERACTION;

EID: 0032560002     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00349-9     Document Type: Article

References (23)

1. 1. (a) Bruno, G. The Use of Aluminum Alkyls in Organic Synthesis, Ethyl Corp. Baton Rouge, 1970.
2. (b) Bruno, G. The Use of Aluminum Alkyls in Organic Synthesis, 1969-1972 Supplement, Ethyl Corp., Baton Rouge, 1973.
3. (c) Honeycutt, J. B. The Use of Aluminum Alkyls in Organic Synthesis, 1972-1978 Supplement, Ethyl Corp., Baton Rouge, 1979.
4. 2. Zweifel, G.; Miller, J. A. Org. React. 1984, 32, 375.
5. 3. Eisch, J. J.; Husk, G. R. J. Org. Chem. 1966, 31, 3419.
6. 4. Swanson, D. R. Ph.D. Dissertation, Purdue University, August, 1991.
7. 5. Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P. Mendeleev Commun. 1992, 135.
8. 6. Negishi, E.; Kondakov, D. Y.; Choueiry, D.; Kasai, K.; Takahashi, T. J. Am. Chem. Soc. 1996, 118, 9577.
9. 7. (a) Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P.; Muslukhov, R. R.; Tostikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 1981.
10. (b) Dzhemilev, U. M.; Ibragimov, A. G.; Azhgaliev, M. N.; Zolotarev, A. P.; Muslukhov, R. R. Russ. Chem. Bull. 1994, 43, 252.
11. 8. Dzhemilev, U. M.; Ibragimov, A. G.; Zolotarev, A. P.; Muslukhov, R. R.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 1071.
12. 9. (a) Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252.
13. (b) Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639.
14. (c) For a review, see Negishi, E. in Comprehensive Organic Synthesis, Vol. 5, Paquette, L. A., Ed., Pergamon, 1991, 1163.
15. 10. For a review of carbonylation of organometals with CO, see Narayana, C.; Periasmy, M. Synthesis 1985, 253.
16. 11. For carbonylation of organozincs, see (a) Rathke, M. W.; Yu, H. J. Org. Chem. 1972, 37, 1732.
17. (b) Knochel, P.; Devasagayaraj, A. Tetrahedron Lett. 1995, 36, 8411.
18. 12. Okukado, N.; Negishi, E. Tetrahedron Lett. 1978, 2357.
19. 2 (99.999%) was directly used.
20. 14. (a) Zhang, Y.; Negishi, E. J. Am. Chem. Soc. 1989, 111, 3454.
21. (b) Owczarczyk, Z.; Lamaty, F.; Vawter, E. J.; Negishi, E. J. Am. Chem. Soc. 1992, 114, 10091.
22. (c) Bailey, W. F.; Tao, Y. Tetrahedron Lett. 1997, 38, 6157.
23. 15. Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R., Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336.