Cooperative Catalysis in Glycosidation Reactions with O‐Glycosyl Trichloroacetimidates as Glycosyl Donors1. Issue 38 (26th July 2013)

• Record Type: Journal Article
• Authors: Geng, Yiqun; Kumar, Amit; Faidallah, Hassan M.; Albar, Hassan A.; Mhkalid, Ibrahim A.; Schmidt, Richard R.
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 38(2013)
• Page Start: 10089
• Page End: 10092
• Publication Date: 2013-07-26
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201302158
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Thiourea mediates cooperative glycosidation</bold> through hydrogen bonding. <italic>N</italic>, <italic>N</italic>′‐Diarylthiourea as cocatalyst enforces an <italic>S</italic>_N2‐type acid‐catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From <italic>O</italic>‐(α‐glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β‐glycosides are preferentially or exclusively obtained.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg37r9m0xd" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>