

IODINE ACETATE AS A MILD SELECTIVE AGENT FOR THE WAGNER–MEERWEIN REARRANGEMENT IN 3a,6-EPOXYISOINDOLES

Abstract
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.
Authors: Vladimir P. Zaytsev*, Dmitriy F. Mertsalov, Anastasiya M. Trunova, Anastasiya V. Khanova, Eugeniya V. Nikitina, Anna А. Sinelshchikova, Mikhail S. Grigoriev
Keywords
cyclopenta[c]pyridines; iodine acetate; isoindoles; IMDAF reaction; intramolecular Diels–Alder reaction; Wagner–Meerwein rearrangement
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv