A Significant Effect of a Lithium Salt in the Stereocontrolled Synthesis of <i>α</i>-<scp>d</scp>-Ribofuranosides

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  • Hiromi Uchiro
    Department of Applied Chemistry, Faculty of Science, Science University of Tokyo
  • Teruaki Mukaiyama
    Department of Applied Chemistry, Faculty of Science, Science University of Tokyo

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<jats:title>Abstract</jats:title> <jats:p>Lithium bis[(trifluoromethyl)sulfonyl]imide was found to be a new and effective additive in the stereocontrolled synthesis of α-d-ribofuranosides from 2,3,5-tri-O-benzyl-d-ribofuranose and several alcohols while β-anomers were formed in the absence of the lithium salt. A hypothetical mechanism of this reverse stereocontrol to yield α-d-ribofuranosides by the influence of the lithium salt is discussed.</jats:p>

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  • Chemistry Letters

    Chemistry Letters 25 (4), 271-272, 1996-04-01

    Oxford University Press (OUP)

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