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. 2013 Sep 16;52(38):10089-92.
doi: 10.1002/anie.201302158. Epub 2013 Jul 26.

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

Yiqun Geng  1 , Amit Kumar, Hassan M Faidallah, Hassan A Albar, Ibrahim A Mhkalid, Richard R Schmidt
Affiliations

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

Yiqun Geng et al. Angew Chem Int Ed Engl. .

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.

Keywords: acid-base catalysis; cooperativity; glycosylation; organocatalysis; thiourea.

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