A cation-catalyzed Wagner–Meerwein skeletal rearrangement in octahydro-2,6a-epoxyoxireno[e]isoindole series was studied. It was shown that the reaction proceeds ambiguously when effected by boron trifluoride etherate in acetic anhydride: the target 4,5-bis(acetoxy)-4,6-epoxycyclopenta[c]pyridines as well as the products of their further degradation, cyclopenta[c]pyridines, were isolated from the reaction mixture in 10–15% yields as single diastereomers.
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The work was supported by the Ministry of Education and Science of the Russian Federation (agreement № 02.a03.21.0008) and the Russian Foundation for Basic Research (RFBR), projects № 16-03-00125 and 16-33-00389.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(9), 736–742
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Zaytsev, V.P., Zubkov, F.I., Nadirova, M.A. et al. Wagner–Meerwein rearrangement in 2,6a-epoxyoxireno[e]isoindole series. Chem Heterocycl Comp 52, 736–742 (2016). https://doi.org/10.1007/s10593-016-1957-9
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DOI: https://doi.org/10.1007/s10593-016-1957-9