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Synlett 1990; 1990(1): 42-43
DOI: 10.1055/s-1990-20980
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Synthesis of γ-Lactones by Iron(III) Perchlorate Oxidation of Malonic Esters in the Presence of Olefins

Attilio Citterio* , Roberto Sebastiano, Marco Nicolini, Roberto Santi
  • *Departimento di Chimica del Politecnico, P.za L. da Vinci 32, I-20133 Milano, Italy
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Publication Date:
08 March 2002 (online)

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Iron(III) perchlorate nonahydrate (FEP) in acetonitrile induces the inter- and intramolecular addition of dialkyl malonates to conjugated olefins (styrenes and dienes) to furnish 3,5,5-trisubstituted 2-oxotetrahydrofuran-3-carboxylic esters 3 in high yield (10 examples). Similar reactions with other olefins give 2-oxotetrahydrofurans (γ-lactones) with lower selectivity.

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