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

• DOI: 10.1007/s10593-016-1957-9
• Publication Date: 2016-11-10T04:19:00Z
• Authors: Vladimir P. Zaytsev; Fedor I. Zubkov; Maryana A. Nadirova; Dmitriy F. Mertsalov; Eugeniya V. Nikitina; Roman A. Novikov; Alexey V. Varlamov
• Keywords: 2,6a-epoxyoxireno[e]isoindoles; 4,6-epoxycyclopenta[c]pyridines; Wagner–Meerwein rearrangement; 540; isoindole; intramolecular Diels–Alder reaction; 01 natural sciences; 0104 chemical sciences

[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.