Regio- and stereospecific cleavage of α,β-epoxysilanes with lithium diphenylphosphide

Tetrahedron Letters

Volumn 38, Issue 46, 1997, Pages 8117-8120

  Cuadrado, Purificación ^a   González Nogal, Ana M ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; LITHIUM SALT; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; METHYLATION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 19244383148     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10123-X     Document Type: Article

References (18)

1. Hudrlik, P.F.; Hudrlik, A.M.; Rona, R.J.; Misra, R.N.; Withers, G.P. J. Am. Chem. Soc. 1977, 99, 1993; Hudrlik, P.F.; Peterson, D.; Rona, R.J. J. Org. Chem. 1975, 40, 2263.
2. Hudrlik, P.F.; Hudrlik, A.M.; Rona, R.J.; Misra, R.N.; Withers, G.P. J. Am. Chem. Soc. 1977, 99, 1993; Hudrlik, P.F.; Peterson, D.; Rona, R.J. J. Org. Chem. 1975, 40, 2263.
3. Fleming, I.; Lawrence, N.J. J. Chem. Soc. Perkin Trans. I 1992, 3309.
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5. Hudrlik, P.F., Peterson, D. Tetrahedron Lett. 1974, 1133; J. Am. Chem. Soc. 1975, 97, 1464.
6. Fleming, I; Newton, T.W. J. Chem. Soc. Perkin Trans. I 1984, 119.
7. Barbero, A.; Cuadrado, P.; Fleming, I.; González, A.M.; Pulido, F.J.; Sánchez, A. J. Chem. Soc. Perkin Trans, I 1995, 1525.
8. Fleming, I.; Newton, T.W.; Roessler, F. J. Chem. Soc. Perkin, Trans, I 1981, 2527.
9. The experimental procedure is the same as that described by García-Martínez, A.; Oliver, M. Synthesis 1983, 663, for converting E-epoxides to Z-olefins.
10. 3CSi).
11. Regiospecific β-opening of a tert-butyldiphenylsilylepoxide has been observed by us in its reaction with methylithium at -25°C (reference ). Other epoxides having hindered silyl groups also undergo β-opening by nucleophiles: Lipshutz, B.H.; Lindsley, C.; Susfalk, R.; Gross, T. Tetrahedron Lett. 1994, 35, 8999.
12. This type of elimination was first proposed by Brook to account for the formation of silyl enol ethers in the reaction of acylsilanes with Wittig reagents: Brook, A.G.; Fieldhouse, S.A. J. Organomet. Chem. 1967, 10, 235.
13. Zbiral, E. In: Organophosphorus Reagents in Organic Synthesis; Cadogan, J.I.G., Ed.; Academic Press: London and New York, 1979, pp. 223-265.
14. For reviews, see: a) Fleming, I. Chimia 1980, 34, 265-271;
15. b) Brownbridge, P. Synthesis 1983, 1-28, 55-104;
16. c) Colvin, E.W. Silicon in Organic Synthesis; Butterworths: London, 1981, pp. 198-287;
17. d) Weber, W.P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlín, 1983; pp. 206-272.
18. 3SiCl led to cis-trans mixtures of silyl enol ethers: Hudrlik, P.F.; Schwartz, R.H.; Kulkarni, A. K. Tetrahedron Lett. 1979, 2233.