化学
酒精氧化
多元醇
酒
酮
有机化学
催化作用
功能群
转移加氢
钌
还原胺化
组合化学
差向异构体
聚合物
聚氨酯
作者
Christopher K. Hill,John F. Hartwig
出处
期刊:Nature Chemistry
[Springer Nature]
日期:2017-08-14
卷期号:9 (12): 1213-1221
被引量:67
摘要
Polyoxygenated hydrocarbons that bear one or more hydroxyl groups comprise a large set of natural and synthetic compounds, often with potent biological activity. In synthetic chemistry, alcohols are important precursors to carbonyl groups, which then can be converted into a wide range of oxygen- or nitrogen-based functionality. Therefore, the selective conversion of a single hydroxyl group in natural products into a ketone would enable the selective introduction of unnatural functionality. However, the methods known to convert a simple alcohol, or even an alcohol in a molecule that contains multiple protected functional groups, are not suitable for selective reactions of complex polyol structures. We present a new ruthenium catalyst with a unique efficacy for the selective oxidation of a single hydroxyl group among many in unprotected polyol natural products. This oxidation enables the introduction of nitrogen-based functional groups into such structures that lack nitrogen atoms and enables a selective alcohol epimerization by stepwise or reversible oxidation and reduction. Polyoxygenated aliphatic chains with multiple hydroxyl groups are common in a wide array of compounds, often with potent biological activity. Now, a new ruthenium catalyst enables selective dehydrogenation of a single hydroxyl group in a broad scope of complex polyols. This site-selective modification facilitates the rapid incorporation of nitrogen-based functional groups into diverse natural products.
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