Abstract
Zinc enolates formed from ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate react under the conditions of one- of two-stage synthesis with aliphatic, unsaturated, or aromatic aldehydes to form 6-R-2,2,4,4-tetramethyl-2,3,5,6-tetrahydropyran-2,4-diones. Zinc enolates obtained from ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate, -hexanoate, and -2,2,5-trimethyl-3-oxohexanoate under the similar conditions react with aliphatic or aromatic aldehydes to give mainly 5-R1-6-R2-3,3-dimethyl-2,3,5,6-tetrahydropyran-2,4-diones as E or Z isomers or their mixtures. Zinc enolates generated from the ethyl 4-bromo-2,2-diethyl- or 2-benzyl-2-ethyl-3-oxobutanoates react with aromatic aldehydes to give ethyl 5-R-2-R-2-ethyl-3-oxo-4-pentenoates as E isomers.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Shchepin, V.V. and Gladkova, G.E., Zh. Org. Khim. 1995, vol. 31, no. 7, p. 1094.
US Patent 4 544 399, 1985, Ref. Zh. Khim. 1986, 13O467P.
US Patent 4 544 399, 1985, Ref. Zh. Khim. 1986, 5O40P.
Australian Patent 560 716, 1987, Ref. Zh. Khim. 1988, 11O433P.
Shchepin, V.V. and Gladkova, G.E., Zh. Org. Khim. 1993, vol. 29, no. 3, p. 474.
Shchepin, V.V., Litvinov, D.N., Russkikh, N.Yu., and Vakhrin, M.I., Zh. Org. Khim. 2000, vol. 36, no. 2, p. 192.
Dewar, M.J.S. and Thiel, W., J. Am. Chem. Soc. 1977, vol. 99, no. 15, p. 4899.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Shchepin, V.V., Sazhneva, Y.K. & Litvinov, D.N. Reaction of Zinc Enolates of Alkyl Esters of Substituted 4-Bromo-3-Oxoalkanoic Acids with Aldehydes. Russian Journal of General Chemistry 73, 596–602 (2003). https://doi.org/10.1023/A:1025600905960
Issue Date:
DOI: https://doi.org/10.1023/A:1025600905960