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Synthesis 2024; 56(07): 1167-1174
DOI: 10.1055/a-2179-8669
DOI: 10.1055/a-2179-8669
paper
Emerging Trends in Glycoscience
Palladium-Catalyzed Stereocontrolled Synthesis of Aryl-C-Glycosides from Arylboronic Acids and Glycal Enones Through 1,4-Conjugate Addition Reactions
J.K. gratefully acknowledges DST-SERB India for the Core Research Grant (CRG/2020/005542).
Abstract
1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-α-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from d-glucal, d-galactal, and d-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.
Key words
glycosides - aryl-C-glycosides - 2-deoxy-aryl-C-glycosides - glycal enones - synthetic methodsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2179-8669.
- Supporting Information
Publication History
Received: 29 August 2023
Accepted after revision: 21 September 2023
Accepted Manuscript online:
21 September 2023
Article published online:
06 November 2023
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