A novel aqueous Barbier-Grignard-type allylation of aldehydes in a Mg/BiCl3 bimetal system

Tetrahedron Letters

Volumn 38, Issue 46, 1997, Pages 8045-8048

  Wada, Makoto ^a   Fukuma, Tomohiro ^a   Morioka, Mika ^a   Takahashi, Toshikazu ^a   Miyoshi, Norikazu ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL ALCOHOL; ORGANOMETALLIC COMPOUND;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0030779719     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10105-8     Document Type: Article

References (36)

1. Part of this work has been presented at the 7th Asian Chemical Congress (7ACC'97) in Hiroshima on May 1997.
2. (a) Hoffman, R.W. Angew. Chem., Int. Ed. Engl. 1982, 21, 555.
3. (b) Yamamoto, Y.; Maruyama, K. Heterocycles. 1982, 18, 357.
4. (c) Yamamoto, Y. Acc. Chem. Res. 1987, 20, 243.
5. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207, and references cited therein.
6. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99.
7. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis. 1989, 787.
8. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p71.
9. (d) Li, C.-J. Chem. Rev. 1993, 93, 2023.
10. (e) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis. 1994, 741.
11. (f) Li, C.-J. Tetrahedron. 1996, 52, 5643.
12. (a) Petrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910.
13. (b) Petrier, C.; Luche, J.-L.; Einhorn, J.; Luche, J. Tetrahedron Lett. 1985, 26, 1449.
14. (c) Einhorn, J.; Luche, J.-L. J. Organomet. Chem. 1987, 322, 177.
15. (d) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697.
16. (e) Wilson, S.R.; Guazzaroni, M.E. J. Org. Chem. 1989, 54, 3087.
17. (f) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics. 1983, 2, 191.
18. (g) Uneyama, K.; Kamaki, N.; Moriya, A.; Torii, S. J. Org. Chem. 1985, 50, 5396.
19. (h) Uneyama, K.; Nambu, H.; Torii, S. Tetrahedron Lett. 1986, 27, 2395.
20. (i) Wu, S.; Huang, B.; Gao, X. Synth. Commun. 1990, 20, 1279.
21. (j) Schmid, W.; Whitesides, G.M. J. Am. Chem. Soc. 1991, 113, 6674.
22. (k) Gao, J.; Harter, R.; Gordon, D.M.; Whitesides, G.M. J. Org. Chem. 1994, 59, 3714.
23. (l) Kim, E.; Gordon, D.M.; Schmid, W.; Whitesides, G.M. J. Org. Chem. 1993, 58, 5500.
24. (m) Li, C.-J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017.
25. (n) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97.
26. (o) Chan, T.-H.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1992, 747.
27. (p) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721.
28. (q) Isaac, M.B.; Chan, T.-H. Tetrahedron Lett. 1995, 36, 8957.
29. 3, Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry. 1996, 7, 1535.
30. 3-Zn, Wang, W.-B.; Shi, L.-L.; Huang, Y.-Z. Tetrahedron. 1990, 46, 3315.
31. (a) Wada, M.; Akiba, K. Tetrahedron Lett. 1985, 26, 4211.
32. (b) Wada, M.; Ohki, H.; Akiba, K. Tetrahedron Lett. 1986, 27, 4771.
33. (c) Wada, M; Ohki, H.; Akiba, K. J. Chem. Soc., Chem. Commun. 1987, 708.
34. (d) Wada, M.; Ohki, H.; Akiba, K. Bull. Chem. Soc. Jpn. 1990, 63, 1738.
35. (e) Wada, M.; Honna, M.; Kuramoto, Y.; Miyoshi, N. Bull. Chem. Soc. Jpn. 1997, in press.
36. Wakefield, B.J. Organomagnesium Methods in Organic Synthesis; Academic Press, 1995.