An ultra-low thiourea catalyzed strain-release glycosylation and a multicatalytic diversification strategy

Chunfa Xu and Charles C. J. Loh ()
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Chunfa Xu: Technische Universität Dortmund,
Charles C. J. Loh: Technische Universität Dortmund,

Nature Communications, 2018, vol. 9, issue 1, 1-12

Abstract: Abstract The utility of thiourea catalysis in selective glycosylation strategies has gained significant momentum lately due to its versatility in hydrogen bonding or anionic recognition activation modes. The use of these non-covalent interactions constitute a powerful means to construct glycosidic linkages as it mimics physiologically occurring glycosyltransferases. However, glycosyl donor activation through the currently employed catalysts is moderate such that, in general, catalyst loadings are rather high in these transformations. In addition, thiourea catalysis has not been well explored for the synthesis of furanosides. Herein, we demonstrate an ultra-low loadings stereoselective and stereospecific thiourea catalyzed strain-release furanosylation and pyranosylation strategy. Our ultra-low organocatalyzed furanosylation enables a multicatalytic strategy, which opens up a unique avenue towards rapid diversification of synthetic glycosides. In-situ NMR monitoring unravel insights into unknown reaction intermediates and initial rate kinetic studies reveal a plausible synergistic hydrogen bonding/Brønsted acid activation mode.

Date: 2018
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DOI: 10.1038/s41467-018-06329-4

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