State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China.
Chem Commun (Camb). 2023 Jun 8;59(47):7279-7282. doi: 10.1039/d3cc01705b.
In this study, we report an organocatalytic formal coupling strategy for aryl-naphthoquinones with thiosugars that provides straightforward access to the axially chiral naphthoquinone thioglycoside with excellent stereoselectivity. Mechanistic studies revealed the key role of H-bonding in stereochemical recognition. The reaction pathway involves the atroposelective addition, followed by stereoretentive oxidation of the hydroquinone intermediate.
在这项研究中，我们报告了一种芳基萘醌与硫代糖的有机催化形式偶联策略，该策略为具有优异立体选择性的轴手性萘醌硫糖苷提供了直接途径。机理研究揭示了氢键在立体化学识别中的关键作用。反应途径包括对映选择性加成，随后是对映体保留的氢醌中间体的氧化。
