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Paper | Regular issue | Vol 63, No. 7, 2004, pp.1573-1576
Published online, 1st June, 2004
DOI: 10.3987/COM-04-10081
Iodoenolcyclization of 2-Allyl Substituted β-Keto Esters under Thermodynamic Conditions

Roberto Antonioletti,* Savina Malancona, and Paolo Bovicelli

*Department of Chemistry, C. N. R. Institute of Biomolecular Chemistry - Roma Section, University “La Sapienza”, Piazzale Aldo Moro 5, I-00185 Roma, Box 34 Roma 62, Italy

Abstract

An improved procedure for the synthesis of diastereo-enriched tetrasubstituted 4,5-dihydrofurans by using I2-induced enolcyclization of β-keto esters is reported. The reactions using I2 in anhydrous MeCN are considered under thermodynamic control and the more stable trans isomers are preferentially produced.