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Communication | Regular issue | Vol 27, No. 1, 1988, pp.17-20
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4312
High Regio- and Stereoselective Cycloaddition of a Nitrone to Alkylidenecyclopropanes

Alberto Brandi,* Silvio Carli, and Andrea Goti

*CNR, Centro di Studio Sulla Chimica e la Struttura dei Composti Eterociclici e lolo Applicazioni, c/o Dipartimento di Chimica Organica "Ugo Schiff", Università di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy


The 1,3-dipolar cycloaddition of 5,5-dimethylpyrroline-N-oxide (DMPO) 3 to methylenecyclopropanes substituted on the exocyclic double bond gives exclusively 4-spirocyclopropane isoxazolines when the substituent is aryl or alkyl group, 5-spirocyclopropane iaoxazolines when the substituent is an electron-withdrawing group. This cyclic nitrone gives cycloadducts with high diastereoselectivity.