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Synlett 1991; 1991(12): 861-862
DOI: 10.1055/s-1991-21986
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Iodo-Atom-Transfer Cyclizations of Δ6,7-Unsaturated 2-Iodo Esters with Chromium(II) Acetate

Thomas Lübbers* , Hans J. Schäfer
  • *Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, D-4400 Münster, Germany
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Publication Date:
07 March 2002 (online)

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Δ6,7-Unsaturated 2-iodo ester 1a and 4-oxa esters 1b-d are cycloisomerized with catalytic amounts of chromium(II) acetate in high yield to substituted cyclopentanes 2 and tetrahydrofurans 3. An inter- and intramolecular radical addition of ethyl 2-iodoacetate (6) to a 1,6-diene 5 (diethyl diallylmalonate) gave in 88 % yield diethyl 3-[2-(ethoxycarbonyl)ethyl]-4-(iodomethyl)-1,1-cyclopentanedicarboxylate (7).

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