Cooperative catalysis in glycosidation reactions with o-glycosyl trichloroacetimidates as glycosyl donors

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Abstract

Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N′-Diarylthiourea as cocatalyst enforces an SN2-type acid-catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O-(α-glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β-glycosides are preferentially or exclusively obtained. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Geng, Y., Kumar, A., Faidallah, H. M., Albar, H. A., Mhkalid, I. A., & Schmidt, R. R. (2013). Cooperative catalysis in glycosidation reactions with o-glycosyl trichloroacetimidates as glycosyl donors. Angewandte Chemie - International Edition, 52(38), 10089–10092. https://doi.org/10.1002/anie.201302158

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