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Paper | Regular issue | Vol 81, No. 12, 2010, pp.2749-2762
Published online, 29th October, 2010
DOI: 10.3987/COM-10-12022
■ Regio- and Stereoselective 1,3-Dipolar Cycloaddition of C-Aryl-N-phenylnitrones over (E)-Arylidene-(2H)-indan-1-ones: Synthesis of Highly Substituted Novel Spiro-isoxazolidines

Nadia Wannassi, Mohamed Mehdi Rammah, Sarra Boudriga, Mohamed El Baker Rammah,* Karin Monnier-Jobé,* Kabula Ciamala, Michael Knorr, Mironel Enescu, Yoann Rousselin, and Marek M. Kubicki

*Department of Chemistry, Laboratory of Heterocyclic Organic Chemistry, Faculty of Sciences, University of Monastir, Avenue Ali Bourguiba, Skanès
5000 Monastir, Tunisia

Abstract

Synthesis of a series of novel spiro-isoxazolidines has been accomplished in good yields by regio- and diastereoselective 1,3-dipolar cycloaddition of (E)-2-arylidene-(2H)-indan-1-ones 1a-d to C-aryl-N-phenylnitrones 2e-h. The structure of the spiro-adducts 3ae-dh was elucidated by 1H and 13C NMR spectroscopy. The proposed regio- and stereochemistry of spiranic compounds 3ae and 3be has been corroborated by two single crystal X-ray crystallographic analyses and by means of DFT calculations.