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Paper | Regular issue | Vol 36, No. 9, 1993, pp.2005-2018
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6376
Functionalized γ-Lactones via Intramolecular Nitrile Oxide Cycloaddition

Giuseppe Buemi, Ugo Chiacchio,* Antonino Corsaro, Giovanni Romeo, Antonio Rescifina, Nicola Uccella, and Alfred Hassner*

*Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel


The intramolecular nitrile oxide cycloaddition of a series of unsaturated hydroxyimino esters has been investigated. The reaction has been found to be stereospecific, with the configuration of the reacting double bond maintained in the final product. Lack of intramolecular pathway has been observed when R, R1 or R2 are hydrogen atoms. AM1 calculation help rationalizes the observed reactions.