Wagner–Meerwein rearrangement in 2,6a-epoxyoxireno[e]isoindole series

[Figure not available: see fulltext.] 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. © 2016, Springer Science+Business Media New York