Organocatalytic atroposelective synthesis of naphthoquinone thioglycosides from aryl-naphthoquinones and thiosugars
Yuling Wu, Wu-Jingyun Zhou, Laiping Yao, Yadi Niu, Hongli Zhao, Cheng Peng, Bo Han, Wei Huang, Gu Zhan
Abstract
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.
Topics & Concepts
NaphthoquinoneChemistryArylStereoselectivityHydroquinoneCombinatorial chemistryStereochemistryOrganic chemistryCatalysisAlkylAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling