Iodine Acetate as a Mild Selective Agent for the Wagner–Meerwein Rearrangement in 3a,6-Epoxyisoindoles

[Figure not available: see fulltext.] The iodine-initiated cationic skeletal Wagner–Meerwein rearrangement in tetrahydro-3a,6-epoxyisoindol-1-ones has been studied. It was shown that by the action of iodine acetate in acetic anhydride the reaction proceeds regio- and stereoselectively with the formation of 5-iodo-4,6-epoxycyclopenta[c]pyridin-4-yl acetates. The proposed reagent provides better yields of rearrangement products than those described in the literature. © 2020, Springer Science+Business Media, LLC, part of Springer Nature.