Metal-free oxidative lactonization of carbohydrates using molecular iodine
Metal-free oxidative lactonization of carbohydrates using molecular iodine
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DOI：
10.1016/j.tet.2013.05.021
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发表时间：
2013-07-22
期刊：
影响因子：
2.1
通讯作者：
Postel, Denis
中科院分区：
文献类型：
--
作者：
Fusaro, Maxime B.;Chagnault, Vincent;Postel, Denis
本文描述了使用分子碘对完全或部分保护的碳水化合物进行氧化内酯化。醛糖半缩醛的氧化通常通过经典方法进行，其很少是化学或区域选择性的。我们最近报道了一种优化的方法，用于氧化酰胺化的醛糖与官能化胺，我们发现分子碘作为一个很好的选择性氧化剂。其他研究小组已经观察到这种性质，但从未研究过碳水化合物的反应范围。该方法的主要优点在于操作简单，无需使用复杂的试剂和程序。(C)2013爱思唯尔有限公司保留所有权利。
We describe herein the oxidative lactonization of fully or partially protected carbohydrates using molecular iodine. Oxidation of aldose hemiacetals is generally carried out by classical procedures, which are rarely chemo or regioselective. We recently reported an optimized methodology for the oxidative amidation of aldose with functionalized amines and we found molecular iodine as a good selective oxidant. This property has been already observed by other research groups but the scope of this reactivity has never been studied for carbohydrates. The main advantage of this approach relies on the operational simplicity, elimination of use of complicated reagents and procedures. (C) 2013 Elsevier Ltd. All rights reserved.