Addition of lithium metal to but-1-en-3-ynes. Synthesis and epoxidation of 1,4-bis(trimethylsilyl)buta-1,2-dienes

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5491-5494

  Santelli Rouvier, Christiane ^a   Lefrère, Sophie ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKYNE DERIVATIVE; LITHIUM;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DERIVATIZATION; DIMERIZATION; EPOXIDATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0033166817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01056-4     Document Type: Article

References (34)

1. For reviews of allene oxide chemistry, see: (a) Stang, P. J. The Chemistry of Functional Groups, Supplement E: The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and their Analogs; Patai, S., Ed.; Wiley: New York, 1983; pp. 859-879.
2. (b) L'Abbé, G. Angew. Chem., Int. Ed. Engl. 1980, 19, 276-289.
3. (c) Jacobs, T. L. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: London, 1982; Vol. 2, pp. 483-491.
4. (d) Smadja, W. Chem. Rev. 1983, 83, 263-320.
5. (a) Camp, R. L.; Greene, F. D. J. Am. Chem. Soc. 1968, 90, 7349.
6. (b) Crandall, J. K.; Conover, W. W.; Komin, J. B.; Machleder, W. H. J. Org. Chem. 1974, 39, 1723-1729.
7. (c) Marshall, J. A.; Tang, Y. J. Org. Chem. 1994, 59, 1457-1464.
8. (d) Behr, H.; Bolte, O.; Draeger, G.; Ries, M.; Schaumann, E. Liebigs Ann. Org. Bioorg. Chem. 1996, 1295-1300.
9. Crandall, J. K.; Machleder, W. H. J. Am. Chem. Soc. 1968, 90, 7347-7349.
10. (a) Crandall, J. K.; Machleder, W. H. J. Am. Chem. Soc. 1968, 90, 7292-7296.
11. (c) Crandall, J. K.; Machleder, W. H.; Sojka, S. A. J. Org. Chem. 1973, 38, 1149-1154.
12. Grimaldi, J.; Bertrand, M. Tetrahedron Lett. 1969, 3269-3272.
13. (b) Grimaldi, J.; Bertrand, M. Bull. Soc. Chim. Fr. 1971, 957-962.
14. The epoxidation of allylallenes can afford bicyclo[3.1.0]hexa-2-ones; see: (a) Grimaldi, J.; Malacria, M.; Bertrand, M. Tetrahedron Lett. 1974, 275-277.
15. (b) Grimaldi, J.; Malacria, M.; Bertrand, M. Bull. Soc. Chim. Fr. 1975, 1725-1730 and 1731-1739.
16. Brash, A. R. J. Am. Chem. Soc. 1989, 111, 1891-1892.
17. (a) Lambert, J. B.; Cheluis, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126.
18. (b) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689.
19. For example, in the silicon-directed Nazarov cyclization, the formation of a silicon stabilized cyclopentenyl cation (an oxyallyl species) led to the exclusive formation of the thermodynamically less stable cyclopentenone isomer; see: (a) Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642-2645.
20. (b) Denmark, S. E.; Klix, R. C. Tetrahedron 1988, 44, 4043-4060.
21. (c) Denmark, S. E.; Habernas, K. L.; Hite, G. A. Helv. Chim. Acta 1988, 71, 168-194.
22. (d) Miesch, M.; Miesch-Gross, L.; Franck-Neumann, M. Tetrahedron 1997, 53, 2103-2110.
23. 2, PhCN, MeOH) led to 2-methyl-5-trimethylsilylcyclopent-2-enone; see: Dulcère, J.-P.; Grimaldi, J.; Santelli, M. Tetrahedron Lett. 1981, 22, 3179-3180.
24. Weyenberg, D. R.; Toporcer, L. H.; Nelson, L. E. J. Org. Chem. 1968, 33, 1975-1982.
25. Tubul, A.; Santelli, M. Tetrahedron 1988, 44, 3975-3982.
26. 3SiCl/Mg/THF afforded 1,6-bis(trimethylsilyl)-2,4-hexadiene; see: Birkofer, L.;Bockhorst, M.; Steigel, A.; Eichstädt, D. J. Organomet. Chem. 1982, 233, 291-297.
27. 3SiCl/Mg/THF afforded 1,6-bis(trimethylsilyl)-2,4-hexadiene; see: Birkofer, L.;Bockhorst, M.; Steigel, A.; Eichstädt, D. J. Organomet. Chem. 1982, 233, 291-297.
28. 4. After filtration, the solvent was removed and the allenic compound was purified.
29. (a) Maercker, A.; Wunderlich, H.; Girreser, U. Tetrahedron 1996, 52, 6149-6172.
30. (b) Maercker, A.; Wunderlich, H.; Girreser, U. Eur. J. Org. Chem. 1998, 793-798.
31. 4. After filtration, the solvent was removed and the compounds were separated by chromatography on silica gel.
32. Stork, G.; Ganem, B. J. Am. Chem. Soc. 1973, 95, 6152-6153.
33. (a) Brook, M. A.; Henry, C.; Jueschke, R.; Modi, P. Synlett 1993, 97-104.
34. (b) Lambert, J. B.; Zhao, Y. J. Am. Chem. Soc. 1996, 118, 7867-7868.