Issue 38, 2024

Construction of thioglycoside bonds via an asymmetric organocatalyzed sulfa-Michael/aldol reaction: access to 4′-thionucleosides

Abstract

Thioglycoside bond formation via an asymmetric sulfa-Michael/aldol reaction of (E)-β-nucleobase acrylketones and 1,4-dithiane-2,5-diol has been achieved with a cinchona alkaloid-derived bifunctional squaramide chiral catalyst. Diverse purine, benzimidazole, and imidazole substrates are well tolerated and generate 4′-thionucleoside derivatives containing three contiguous stereogenic centers with excellent results (30 examples, up to 97% yield, >20 : 1 dr and up to 99% ee). Moreover, the novel strategy provides an efficient and convenient synthetic route to construct chiral 4′-thionucleosides.

Graphical abstract: Construction of thioglycoside bonds via an asymmetric organocatalyzed sulfa-Michael/aldol reaction: access to 4′-thionucleosides

Supplementary files

Article information

Article type
Communication
Submitted
01 mar 2024
Accepted
08 apr 2024
First published
08 apr 2024

Chem. Commun., 2024,60, 5018-5021

Construction of thioglycoside bonds via an asymmetric organocatalyzed sulfa-Michael/aldol reaction: access to 4′-thionucleosides

T. Wei, M. Xie and H. Guo, Chem. Commun., 2024, 60, 5018 DOI: 10.1039/D4CC00984C

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