Iron(iii) chloride-catalyzed activation of glycosyl chloridesElectronic supplementary information (ESI) available: Experimental details and characterization data for all new compounds. See DOI: 10.1039/c8ob02413h

Glycosyl chlorides have historically been activated using harsh conditions and/or toxic stoichiometric promoters. More recently, the Ye and the Jacobsen groups showed that glycosyl chlorides can be activated under organocatalytic conditions. However, those reactions are slow, require specialized cat...

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Main Authors: Geringer, Scott A, Demchenko, Alexei V
Format: Article
Language:English
Online Access:Get full text
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Summary:Glycosyl chlorides have historically been activated using harsh conditions and/or toxic stoichiometric promoters. More recently, the Ye and the Jacobsen groups showed that glycosyl chlorides can be activated under organocatalytic conditions. However, those reactions are slow, require specialized catalysts and high temperatures, but still provide only moderate yields. Presented herein is a simple method for the activation of glycosyl chlorides using abundant and inexpensive ferric chloride in catalytic amounts. Our preliminary results indicate that both benzylated and benzoylated glycosyl chlorides can be activated with 20 mol% of FeCl 3 . Glycosyl chlorides can be readily activated with 20 mol% of FeCl 3 .
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02413h