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An Expedient Method for Kinetically Controlled Acetonide Formation from d-Fructose Induced by Ionic Liquid Catalyst Accompanied with SrCl2·6H2O

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Abstract

The present work was undertaken to ascertain whether IL-metal salt catalyzed isopropylidenation of d-fructose yield desired acetonides. For the first time, an imidazole based ionic liquid compound accompanied with strontium chloride has been identified as a suitable dual catalyst system for the chemoselective O-isopropylidenation of d-fructose with acetone. In the present protocol, mainly the kinetically controlled less stable cyclic ketal 1,2;4,5-di-O-isopropylidene-β-d-fructopyranose is formed as an initial product with satisfactory yield and without isomerization to the thermodynamically more stable cyclic ketal 2,3;4,5-di-O-isopropylidene-β-d-fructopyranose. Therefore, this protocol is more advantageous compared to other mineral acid catalyzed protocols that require more sensitive reaction conditions.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Bursa Uludağ University, Bursa, Turkey

    Ayhan Yıldırım

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  1. Ayhan Yıldırım
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Correspondence to Ayhan Yıldırım.

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Yıldırım, A. An Expedient Method for Kinetically Controlled Acetonide Formation from d-Fructose Induced by Ionic Liquid Catalyst Accompanied with SrCl2·6H2O. Catal Lett 150, 2566–2571 (2020). https://doi.org/10.1007/s10562-020-03175-2

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  • DOI: https://doi.org/10.1007/s10562-020-03175-2

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