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Synthesis 2024; 56(07): 1167-1174
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

Adesh Kumar Singh
a   Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, India-221005, India
,
Rapelly Venkatesh
b   Department of Chemistry, Pondicherry University, Kalapet, Pondicherry, India-605014, India
,
Jeyakumar Kandasamy  ∗
a   Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, India-221005, India
b   Department of Chemistry, Pondicherry University, Kalapet, Pondicherry, India-605014, India
› Author AffiliationsJ.K. gratefully acknowledges DST-SERB India for the Core Research Grant (CRG/2020/005542).
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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 methods

Supporting 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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