Abstract
Sodium derivative of diethyl(3-amino-1-ethoxycarbonylpropane)phosphonic acid was obtained by reaction of triethyl phosphonoacetate with ethylene imine in the presence of sodium hydride. The compound obtained was brought into Horner-Emmons reaction with carbonyl derivatives of adamantane series to afford the corresponding unsaturated amino acids. From adamantanecarbonyl chlorides and triphenylphosphonium ethoxycarbonylmethylide were prepared new phosphorus acylylides that on thermolysis provide ethyl acetylenecarboxylates containing an adamantyl substituent.
Similar content being viewed by others
REFERENCES
Miryan, N.I., Isaev, S.D., Kovaleva, S.A., Petukh, N.V., Dvornikova, E.V., Kardakova, E.V., and Yurchenko, A.G., Zh. Org. Khim. 1999, vol. 35, no. 6, pp. 882-886.
Hiene, H.W., Lowrie, H.B., Irving, R.C., J. Org. Chem. 1970, vol. 35, no. 2, pp. 444-447.
Kolodyazhnyi, O.I. Khimiya ilidov fosfora (Chemistry of Phosphorus Ylides), Kiev: Naukova Dumka, 1994.
Markl, G., Angew. Chem. 1962, vol. 74, no. 6.
Bestmann, H.J., Kumar, K, and Schafer, W., Angew. Chem. 1983, vol. 95, no. 2, p. 154.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Miryan, N.I., Isaev, S.D., Yurchenko, A.G. et al. Synthesis of Unsaturated Carboxylic and Amino Acids of Adamantane Series with the Use of Organophosphorus Reagents. Russian Journal of Organic Chemistry 38, 188–190 (2002). https://doi.org/10.1023/A:1015501313852
Issue Date:
DOI: https://doi.org/10.1023/A:1015501313852