WAGNER–MEERWEIN REARRANGEMENT IN 2,6a-EPOXYOXIRENO[ e ]ISOINDOLE SERIES
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. Authors: Vladimir P. Zaytsev*, Fedor I. Zubkov, Mar'yana A. Nadirova, Dmitriy F. Mertsalov, Eugeniya V. Nikitina, Roman A. Novikov, Alexey V. Varlamov