Barbier-type allylation of carbonyl derivatives by use of aluminum as an electron pool. Double allylation of carboxylic esters

Inorganica Chimica Acta

Volumn 296, Issue 1, 1999, Pages 204-207

  Tanaka, Hideo ^b   Nakahata, Sigeru ^b   Watanabe, Hiroshi ^b   Zhao, Jinfeng ^b   Kuroboshi, Manabu ^b   Torii, Sigeru ^a,b  

^a Institute of Creative Chemistry Co   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

Allylation; Aluminum metal; Barbier type allylation; Double allylation of carboxylic ester; Lead(II) salts

Indexed keywords

ALLYLATION; ALUMINUM; AROMATIC COMPOUNDS; DIMETHYLFORMAMIDE; ESTERS; ETHERS; ORGANIC SOLVENTS;

ALLYLATION PRODUCTS; ALUMINUM METAL; BARBIER TYPE; CARBONYL DERIVATIVES; CARBOXYLIC ESTERS; CATALYTIC AMOUNTS; N ,N-DIMETHYLFORMAMIDE; TETRAHYDROFURANS;

LEAD COMPOUNDS;

EID: 0001589605     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0020-1693(99)00393-X     Document Type: Article

References (30)

1. For reviews: (a) G. Courtois, L. Miginiac, J. Organomet. Chem. 69 (1974) 1. (b) J.F. Biellmann, J.B. Ducep, Org. React. 27(1982) 1. (c) R.W. Roush, in: B.M. Trost, I. Fleming, C.H. Heathcock (Eds.), Comprehensive Organic Synthesis, vol. 2, Pergamon, Oxford, UK, 1991, p. 1.
2. For reviews: (a) G. Courtois, L. Miginiac, J. Organomet. Chem. 69 (1974) 1. (b) J.F. Biellmann, J.B. Ducep, Org. React. 27(1982) 1. (c) R.W. Roush, in: B.M. Trost, I. Fleming, C.H. Heathcock (Eds.), Comprehensive Organic Synthesis, vol. 2, Pergamon, Oxford, UK, 1991, p. 1.
3. For reviews: (a) G. Courtois, L. Miginiac, J. Organomet. Chem. 69 (1974) 1. (b) J.F. Biellmann, J.B. Ducep, Org. React. 27(1982) 1. (c) R.W. Roush, in: B.M. Trost, I. Fleming, C.H. Heathcock (Eds.), Comprehensive Organic Synthesis, vol. 2, Pergamon, Oxford, UK, 1991, p. 1.
4. (a) P.J. Pearce, D.H. Richard, N.F. Scilly, J. Chem. Soc., Perkin 1 (1971) 1655.
5. (b) J.L. Luche, J.C. Damiano, J. Am. Chem. Soc. 102 (1980) 7927.
6. C. Blomberg, F.A. Hartog, Synthesis (1977) 18.
7. (a) T. Hiyama, M. Obayashi, A. Nakamura, Organometallics 1 (1982) 1249.
8. (b) T. Hiyama, M. Sawahata, Y. Kusano, Chem. Lett. (1985) 611.
9. (a) T. Hiyama, M. Sawahata, M. Obayashi, Chem. Lett. (1983) 1237.
10. (b) G.P. Boldrini, D. Savoia, E. Tagliavini, C. Trombin, A. Umani-Ronchi, J. Org. Chem. 48 (1983) 4108.
11. (c) C. Perier, J.L. Luche, J. Org. Chem. 50 (1985) 910.
12. (d) C. Peter, J. Einhorn, J.L. Luche, Tetrahedron Lett. 26 (1985) 1449.
13. (a) T. Mukaiyama, T. Warada, S. Shoda, Chem. Lett. (1980) 1207.
14. (b) J. Nokami, J. Otera, T. Sudo, R. Okawara, Organometallics 2 (1983) 191.
15. H. Tanaka, S. Yamashita, T. Hamatani, Y. Ikemoto, S. Torii, Chem. Lett. (1986) 1611.
16. (a) M. Wada, K. Akiba, Tetrahedron Lett. 26 (1985) 4211.
17. (b) M. Wada, H. Ohki, K. Akiba, Tetrahedron Lett. 27 (1986) 4771.
18. (c) M. Wada, H. Ohki, K. Akiba, J. Chem. Soc., Chem. Commun. (1987) 708.
19. T. Imamoto, T. Kusumoto, Y. Tawarayama, Y. Sugiura, T. Mita, J. Org. Chem. 49 (1984) 3904.
20. (a) Y. Okude, S. Hirano, T. Hiyama, H. Nozaki, J. Am. Chem. Soc. 99 (1977) 3179.
21. (b) C.T. Buse, C.H. Heathcock, Tetrahedron Lett. 19 (1978) 1685.
22. (c) J. Souppe, J.L. Namy, B.H. Kagan, Tetrahedron Lett. 23 (1982) 3497.
23. (d) Y. Butugan, H. Ito, S. Araki, Tetrahedron Lett. 28 (1987) 3707.
24. J.F. Ruppert, J.D. White, J. Org. Chem. 41 (1976) 550, see also Refs. [3] and [9].
25. K. Uneyama, N. Kamaki, A. Moriya, S. Torii, J. Org. Chem. 50 (1985) 5396.
26. H. Tanaka, S. Yamashita, T. Hamatani, Y. Ikemoto, S. Torii, Synth. Commun. 17 (1987) 789.
27. (a) H. Tanaka, S. Yamashita, Y. Ikemoto, S. Torii, Tetrahedron Lett. 29 (1988) 1721.
28. (b) H. Tanaka, K. Inoue, U. Pokorski, M. Taniguchi, S. Torii, Tetrahedron Lett. 31 (1990) 3023.
29. H. Tanaka, S. Yamashita, Y. Ikemoto, S. Torii, Chem. Lett. (1987) 673.
30. V. Gutmann, E. Wychera, Inorg. Nucl. Chem. Lett. 2 (1966) 257.