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Ferrier Rearrangement and 2-Deoxy Sugar Synthesis from d-Glycals Mediated by Layered α-Zirconium Sulfophenylphosphonate-Methanphosphonate as Heterogeneous Catalyst

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Abstract

Layered α-zirconium sulfophenylphosphonate-methanphosphonate is a solid acid catalyst that catalyzes Ferrier rearrangement from d-glycals and alcoholic nucleophiles under mild reaction conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate-methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.

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Acknowledgments

Financial support from MIUR, National Project “Approccio ecocompatibile all’intensificazione di processo nella sintesi organica” is gratefully acknowledged.

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Authors and Affiliations

  1. Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, via del Liceo 1, 06123, Perugia, Italy

    Ornelio Rosati, Massimo Curini, Federica Messina & Maria Carla Marcotullio

  2. Dipartimento di Scienza e Tecnologia del Farmaco, Università degli Studi di Torino, Via P. Giuria 9, 10125, Torino (TO), Italy

    Giancarlo Cravotto

Authors
  1. Ornelio Rosati
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  2. Massimo Curini
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  3. Federica Messina
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  4. Maria Carla Marcotullio
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  5. Giancarlo Cravotto
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Correspondence to Ornelio Rosati.

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Rosati, O., Curini, M., Messina, F. et al. Ferrier Rearrangement and 2-Deoxy Sugar Synthesis from d-Glycals Mediated by Layered α-Zirconium Sulfophenylphosphonate-Methanphosphonate as Heterogeneous Catalyst. Catal Lett 143, 169–175 (2013). https://doi.org/10.1007/s10562-012-0932-z

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  • DOI: https://doi.org/10.1007/s10562-012-0932-z

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