Migration of trimethylsilyl groups in enolates of silyl esters

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4029-4032

  Hudrlik, Paul F ^a   Roberts, Ralph R ^a   Ma, Da ^a   Hudrlik, Anne M ^a  

^a HOWARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; FUNCTIONAL GROUP; LITHIUM DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030921273     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00864-2     Document Type: Article

References (26)

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4. (b) Bellassoued, M.; Gaudemar, M. Tetrahedron Lett. 1990, 31, 209-212.
5. 3N, THF, reflux 10 h).
6. Products were isolated by filtration and concentration on the rotary evaporator without aqueous workup.
7. +, 78).
8. 3N, THF, reflux 3 h).
9. +, 50). See also Shchukovskaya, L. L.; Pal'chik, R. I.; Lazarev, A. N. Doklady Chem. 1965, 164, 887-890.
10. +, 58), 59 (56), 45 (47).
11. +, 48).
12. +, 45).
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16. Soderquist, J. A.; Rivera, I.; Negron A. J. Org. Chem. 1989, 54, 4051-4055.
17. 13C NMR.
18. For leading references on anionic rearrangements of silyl groups, see: (a) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States, Vol. 2; de Mayo, P., Ed.; Academic Press: New York, 1980, pp. 149-227.
19. (b) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213-4227. For base-catalyzed rearrangements of silylacetic acids to give acyloxysilanes, see:
20. (c) Brook, A. G.; Anderson, D. G.; Duff, J. M. J. Am. Chem. Soc. 1968, 90, 3876-3877. For recent examples of 1,3 O → C silyl migrations, see:
21. (d) Baudrillard, V.; Plé, G.; Davoust, D. J. Org. Chem. 1995, 60, 1473-1474.
22. (e) He, H.-M.; Fanwick, P. E.: Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905-5909.
23. - (Raucher, S.; Schindele, D. C. Synth. Commun. 1987, 17, 637-646). The formation of acyloxysilanes (4a and 4b) may have been due to partial hydrolysis of silyl ketene acetals.
24. 2SiCl gave a mixture of products containing 3, consistent with an intermolecular silylation reaction: Nietzschmann, E.; Böge, O.; Tzschach, A. J. Prakt. Chem. 1991, 333, 281-284.
25. For recent examples, see: (a) Bellassoued, M.; Dubois, J. E.; Bertounesque, E. Synth. Commun. 1987, 17, 1181-1183.
26. (b) Bellassoued, M.; Dubois, J. E.; Bertounesque, E. Bull. Soc. Chim. Belg. 1988, 97, 263-266.