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Abs mbr+wannassi+mmr het 2010


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Abs mbr+wannassi+mmr het 2010

  1. 1. Abstract Paper Volume 81, Issue 12 ( December, 1, 2010 ), Pages 2749-2762 Received, 17th July, 2010, Accepted, 21st October, 2010, Published online, 29th October, 2010. DOI: 10.3987/COM-10-12022 Full Text HTML PDF (942KB) PDF with Links (1.4MB) 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 MonnierJobé,* Kabula Ciamala, Michael Knorr, Mironel Enescu, Yoann Rousselin, and Marek M. Kubicki Institute of UTINAM UMR CNRS 6213, Faculty of Science and Technology, University of Franche-Comté, 16 Route de Gray, F-25030 Besançon, France 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 1 13 2e-h. The structure of the spiro-adducts 3ae-dh was elucidated by H and C NMR spectroscopy. The proposed regio- and stereochemistry of spiranic compounds 3ae and 3be has been corroborated by two single crystal Xray crystallographic analyses and by means of DFT calculations. Graphical Abstract Keywords 1. Nitrone 2. Spiroisoxazolidine 3. Regioselectivity 4. Stereoselectivity 5. Cycloaddition Corresponding author; email: Mail to us | Privacy Statement | Copyright © 2011 The Japan Institute of Heterocyclic Chemistry | Recommend to your Librarian