Abstract
Acylation of silylenol ethers1 and9 yield with 2-alkoxy-2-alkyl(or aryl)-1,3-dioxolanes5 in a simple way by zinc dichloride-diethyl ether-catalysis regioselectively the α- and γ-protected dicarbonyl derivatives6,7, and10. The enhanced reactivity of the cyclic orthoesters5 in this reaction is discussed in comparison with acyclic reagents. The yield is influenced by steric effects at the reaction center.
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Literatur
1. Mitt.:Akgün E., Pindur U., Chem.-Ztg.107, 236 (1983).
2. Mitt.:Akgün E., Pindur U., Chem.-Ztg.107, 237 (1983).
Fleming I., Frontier Orbitals and Organic Chemical Reactions, S. 43 ff. Chichester-New York-Brisbane-Toronto: Wiley & Sons. 1976.Noyori R., Nishida I., Sakata J., J. Amer. Chem. Soc.105, 1598 (1983).
Chiang Y., Kresge A. J., Salomaa P., Young C. J., J. Amer. Chem. Soc.96, 4494 (1974).
Paulsen H., Dammeyer R., Chem. Ber.106, 2324 (1973).
Bouab O., Lamaty G., Moreau C., Pomares O., Deslongchamps P., Ruest L., Can. J. Chem.58, 567 (1980).
Hünig S., Angew. Chem.76, 400 (1964); Angew. Chem. Int. Ed. Engl.3, 548 (1964).
Holmes J. L., Lossing F. P., Can. J. Chem.60, 2365 (1982).
Akgün E., Diplomarbeit, Univ. Marburg, 1977.
Fleming I., Iqbal J., Krebs E.-P., Tetrahedron39, 841 (1983).Paterson I., Price L. G., Tetrahedron Lett.1981, 2833.Fleming I., Lee T. V., Tetrahedron Lett. 1981, 705.Mukaiyama T., Ishida A., Chem. Lett.1975, 319.
Alston P. V., Ottenbrite R. M., J. Org. Chem.40, 1111 (1975).
Williams D. H., Fleming G., Spektroskopische Methoden in der Organischen Chemie, S. 63. Stuttgart: G. Thieme. 1971.
Levy G. C., Lichter R. L., Nelson G. L., Carbon-13-Nuclear Magnetic Resonance Spectroscopy, S. 141. New York-Chichester-Brisbane-Toronto: Wiley. 1980.
Taft R. W., Martin R. H., Lampe R. W., J. Amer. Chem. Soc.87, 2490 (1965); ibid.88, 1353 (1966).
Mukaiyama T., Angew. Chem.89, 858 (1977).
Emde H.,Götz A.,Hofmann K.,Simchen G., Liebigs Ann. Chem.1981, 1643.
Aldrich Company, 22, 722–726.
House H. O., Crumrine D. S., Teranishi A. Y., Olmstead H. D., J. Amer. Chem. Soc.95, 3310 (1973).
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Akgün, E., Pindur, U. Silylenolether-Funktionalisierung, 3. Mitt. Regioselektive Acylierung von Trimethylsilylenolethern mit 2-Alkoxy-1,3-dioxolanen — Synthese von α- und γ-geschützten Dicarbonylverbindungen. Monatsh Chem 115, 587–595 (1984). https://doi.org/10.1007/BF00799167
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DOI: https://doi.org/10.1007/BF00799167