Abstract
Electrophilic cyclization initiated by NBS and I2 of 2,2-dichloro-2-[(1R,5S)- and 2,2-dichloro-2-[(1S,5R)-5-hydroxy-2-cyclopent-2-en-1-yl]-N-[(1R)-1-phenylethyl]acetamides was investigated. Stable under conditions of chromatography on SiO2 bicyclic iminoesters, (2Z,3aS,4S,6S,6aS)-6-bromo-3,3-dichloro- and (2Z,3aS,4S,6S,6aS)-3,3-dichloro-6-iodo-2-{[(1R)-1-phenylethyl]imino}hexahydro-2H-cyclopenta[b]furan-4-ols were isolated and characterized, and a possible version was suggested of their step-by-step recyclization transformations. The halocyclization of carboxamides in water-organic mixtures afforded bicyclic epoxylactones (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-5,5-dichlorohexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones, whose reductive dechlorination proceeded stepwise with successive removal of Cl atoms and led to the formation of (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-hexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones.
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Original Russian Text © Z.R. Valiullina, V.A. Akhmet’yanova, N.A. Ivanova, A.S. Erastov, E.S. Meshcheryakova, M.S. Miftakhov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 11, pp. 1558–1564.
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Valiullina, Z.R., Akhmet’yanova, V.A., Ivanova, N.A. et al. Haloiminolactonization of cyclopentene α,α-dichlorocarboxamides. Tandem rearrangement of iminolactones in epoxylactones. Russ J Org Chem 51, 1524–1531 (2015). https://doi.org/10.1134/S1070428015110020
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DOI: https://doi.org/10.1134/S1070428015110020