Diisobutylaluminum Hydride Mediated Regioselective O Desilylations: Access to Multisubstituted Cyclodextrins

Authors

  • Dr. Ramprasad Ghosh,

    1. Alberta Ingenuity Centre for Carbohydrate Science, Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary Alberta T2N 1N4 (Canada)
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  • Dr. Ping Zhang,

    1. Alberta Ingenuity Centre for Carbohydrate Science, Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary Alberta T2N 1N4 (Canada)
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  • Dr. Aixia Wang,

    1. Alberta Ingenuity Centre for Carbohydrate Science, Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary Alberta T2N 1N4 (Canada)
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  • Prof. Dr. Chang-Chun Ling

    Corresponding author
    1. Alberta Ingenuity Centre for Carbohydrate Science, Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary Alberta T2N 1N4 (Canada)
    • Alberta Ingenuity Centre for Carbohydrate Science, Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary Alberta T2N 1N4 (Canada)
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  • We thank the Alberta Ingenuity (now part of Alberta Innovates–Technology Futures) and the University of Calgary for the financial support of current project. C.C.L. thanks the Canadian Foundation for Innovation and the Government of Alberta for the Leadership Opportunity Award.

Abstract

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A face off: Diisobutylaluminum hydride (DIBAL-H) has been found to be an effective O-desilylating reagent at the primary face of cyclodextrins. This methodology shows high chemo- and regioselectivity and provides an effective route to orthogonally protected, multisubstituted cyclodextrin derivatives.

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