Abstract
Methyl (E)-3-[(4S,5S)-5-acetyl-2,2-dimethyl-1,3-dioxolan-4-yl)]prop-2-enoate obtained from D-ribose eliminates water on storage and transforms into a bicyclic crystalline “dimer”.
REFERENCES
Simeonov, S.P., Nunes, J.P.M., Guerra, K., and Kurteva, V.B., Chem. Rev., 2016, vol. 116, p. 5744. https://doi.org/10.1021/cr500504w
Johnson, C.R. and Chen, Y.F., J. Org. Chem., 1991, vol. 56, p. 3344. https://doi.org/10.1021/jo00010a031
Elhalem, E., Comin, M.J., Leitofuter, J., and Garcia-Linares, G., Tetrahedron Asymmetry, 2005, vol. 16, p. 425. https://doi.org/10.1016/j.tetasy.2004.11.069
Gallos, J.K., Stathakis, C.I., Kotoulas, S.S., and Koumbis, E., J. Org. Chem., 2005, vol. 70, p. 6884. https://doi.org/10.1021/jo050987t
Ivanova, N.A., Valiullina, Z.R., Shitikova, O.V., and Miftakhov, M.S., Russ. J. Org. Chem., 2007, vol. 43, p. 742. https://doi.org/10.1134/S1070428007050168
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A.V., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H.P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery, J.A. Jr., Peralta, J.E., Ogliaro, F., Bearpark, M.J., Heyd, J.J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Keith, T.A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., and Fox, D.J., Gaussian 09, Revision C.01, Gaussian, Inc, Wallingford CT, 2010.
Knunyants, I.L., Uspekhi organicheskoi khimii (Advances in Organic Chemistry), Moscow: Inostrannaya Literatura, 1963, vol. 1.
Gordon, A. and Ford, R., Sputnik khimika, Moscow: Mir, 1976.
ACKNOWLEDGMENTS
Analytical measurements were performed using the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences.
Funding
The work was performed by the state order (contract no. AAAA-A20-120012090021-4).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
Valiullina, Z.R., Ivanova, N.A., Lobov, A.N. et al. Regioselective Intermolecular Cyclization of Methyl (E)-3-[(4S,5S)-5-Acetyl-2,2-dimethyl-1,3-dioxolan-4-yl)]prop-2-enoate. Russ J Org Chem 56, 2043–2047 (2020). https://doi.org/10.1134/S1070428020110226
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428020110226