Department of Chemistry and Biochemistry, University of Missouri - St Louis, One University Boulevard, St Louis, Missouri 63121, USA.
Org Biomol Chem. 2018 Dec 5;16(47):9133-9137. 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 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 FeCl3.
糖基氯化物在历史上是通过苛刻的条件和/或有毒的化学计量促进剂来激活的。最近，Ye 和 Jacobsen 小组表明，糖基氯化物可以在有机催化条件下被激活。然而，这些反应速度较慢，需要特殊的催化剂和高温，而且仍然只能提供中等的产率。本文提出了一种使用丰富且廉价的氯化铁作为催化剂来激活糖基氯化物的简单方法。我们的初步结果表明，苄基化和苯甲酰化的糖基氯化物都可以用 20mol%的三氯化铁激活。
