Issue 47, 2023

Organocatalytic atroposelective synthesis of naphthoquinone thioglycosides from aryl-naphthoquinones and thiosugars

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.

Graphical abstract: Organocatalytic atroposelective synthesis of naphthoquinone thioglycosides from aryl-naphthoquinones and thiosugars

Supplementary files

Article information

Article type
Communication
Submitted
06 Apr 2023
Accepted
12 May 2023
First published
19 May 2023

Chem. Commun., 2023,59, 7279-7282

Organocatalytic atroposelective synthesis of naphthoquinone thioglycosides from aryl-naphthoquinones and thiosugars

Y. Wu, W. Zhou, L. Yao, Y. Niu, H. Zhao, C. Peng, B. Han, W. Huang and G. Zhan, Chem. Commun., 2023, 59, 7279 DOI: 10.1039/D3CC01705B

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