A convenient allylation of 1,n-dicarbonyl compounds using organoindium reagents

Bulletin of the Korean Chemical Society

Volumn 22, Issue 12, 2001, Pages 1380-1384

  Lee, Phil Ho ^a   Seomoon, Dong ^a   Lee, Kooyeon ^a  

^a Kangwon National University   (South Korea)

Author keywords

Allylindium reagent; Chemoselectivity; Hydroxy unsaturated carbonyl compounds; Indium

Indexed keywords

2,3 BUTANEDIONE; CARBONYL DERIVATIVE; HALIDE; INDIUM; LEVULINIC ACID; PYRUVIC ACID; REAGENT;

ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0035924896     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. (a) Trost, B. M. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; p 1.
2. (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
3. (a) Yamamoto, Y. Acc. Chem. Res. 1987, 20, 243.
4. (b) Hoffmann, R. W. Angew. Chem. Int. Ed. Engl. 1982, 21, 555.
5. (c) Yamamoto, Y.; Maruyama, K. Heterocycles 1982, 18, 357.
6. (d) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1.
7. (a) Li, C.-J. Tetrahedron 1996, 52, 5643.
8. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
9. (c) Li, C.-J. Chem. Rev. 1993, 93, 2023.
10. (d) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149.
11. (e) Li, C.-J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017.
12. (f) Isaac, M. B.; Chan, T.-H. Tetrahedron Lett. 1995, 36, 8957.
13. (g) Beuchet, P.; Marrec, N. L.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959.
14. (h) Loh, T-P.; Ho, D. S.; Xu, K.-C.; Sim, K.-Y. Tetrahedron Lett. 1997, 38, 865.
15. (i) Chan, T.-H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605.
16. (a) Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500.
17. (b) Bindra, W. H.; Prenner, R. H.; Schmid, W. Tetrahedron 1994, 50, 749.
18. (c) Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228.
19. (d) Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry 1996, 7, 1535.
20. (e) Loh, T.-P.; Ho, D. S.-C.; Chua, G.-L.; Sim, K.-Y. Synlett 1977, 563.
21. (f) Yi, X.-H.; Meng, Y.; Li, C.-J. Chem. Commun. 1988, 449.
22. (g) Li, C.-J.; Lu, Y.-Q. Tetrahedron Lett. 1995, 36, 2721.
23. (h) Nair, V.; Jayan, C. N. Tetrahedron Lett. 2000, 41, 1091.
24. (i) Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. Tetrahedron 1998, 54, 2347.
25. (j) Paquette, L. A.; Isaac, M. B. Heterocycles 1998, 47, 107.
26. (a) Lee, P. H.; Ahn, H.; Lee, K.; Sung, S.-Y.; Kim, S. Tetrahredron Lett. 2001, 42, 37.
27. (b) Lee, P. H.; Lee, K.; Kim, S. Org. Lett. 2001, 3, 3205.
28. (c) Lee, P. H.; Sung, S.Y.; Lee, K. Org. Lett. 2001, 3, 3201.
29. For a preliminary account of this work, Lee, P. H.; Lee, K.; Chang, S. Synth. Commun. 2001, 31, 3189.
30. 13C-NMR, MS, and IR spectroscopy.
31. 4-Bromo-3-[(trimethylsilyl)methyl]-1,2-butadiene was prepared from 2-butyn-1,4-diol according to the following scheme.