Organometallic-type reactions in aqueous media mediated by indium. Allylation of acyloyl-imidazoles and pyrazoles. Regioselective synthesis of β,γ-unsaturated ketones.

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6493-6496

  Bryan, Vernal J ^a   Chan, Tak Hang ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; INDIUM; KETONE DERIVATIVE; ORGANOMETALLIC COMPOUND; PYRAZOLE DERIVATIVE; TERPENE;

AQUEOUS SOLUTION; ARTICLE; SYNTHESIS;

ARTEMESIA;

EID: 0030880655     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01512-8     Document Type: Article

References (14)

1. (a) Chan, T. H.; Li, C. J.; Wei, J. Y.; Lee, M. C., Can. J. Chem., 1994, 72, 1181;
2. (b) Li, C. J., Chem. Rev., 1993, 93, 2023;
3. (c) Chan, T. H.; Isaac, M. B., Pure & Appl. Chem., 1996, 68, 919.
4. Li, C. J.; Chan, T. H., Tetrahedron Lett., 1991, 32, 7017.
5. Loh, T.-P.; Li, X.-R., Tetrahedron Lett., 1997, 38, 869 and references cited therein.
6. Bryan, V. J.; Chan, T. H., Tetrahedron Lett., 1996, 37, 5341.
7. (a) Chan, T. H.; Li, C. J., J. Chem. Soc., Chem. Commun., 1992, 747;
8. (b) Chan, T. H.; Lee, M. C., J. Org. Chem., 1995, 60, 4228;
9. (c) Chan, T. H.; Xin, Y.-C., J. Chem. Soc., Chem. Commun., 1996, 905;
10. (d) Gao, J.; Martichonok, V.; Whitesides, G. M., J. Org. Chem., 1996, 61, 9538.
11. Issac, M. B.; Chan, T. H., Tetrahedron Lett., 1995, 36, 8957.
12. Reactions of allylindium reagents with acid anhydrides in organic solvents had been reported. Araki, S.; Katsumura, N,; Ito, H.; Nitsigam, Y. Tetrahedron Lett. 1989, 30, 1581. We found that benzoyl chloride reacted under similar conditions to give complex mixtures.
13. Zalkow, L. H.; Brannon, D. R.; Uecke, J. W. J. Org. Chem., 1964, 29, 2786.
14. For previous synthesis, see Pillot, J.-P.; Dunogues, J.; Calas, R. Tetrahedron Lett., 1976, 1871.