Palladium-Catalyzed Stereocontrolled Synthesis of Aryl-C-Glycosides from Arylboronic Acids and Glycal Enones Through 1,4-Conjugate Addition Reactions

Adesh Kumar Singh; Rapelly Venkatesh; Jeyakumar Kandasamy

doi:10.1055/a-2179-8669

Synthesis, Table of Contents

Synthesis 2024; 56(07): 1167-1174
DOI: 10.1055/a-2179-8669

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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

^aDepartment of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, India-221005, India

,

Rapelly Venkatesh

^bDepartment of Chemistry, Pondicherry University, Kalapet, Pondicherry, India-605014, India

,

Jeyakumar Kandasamy ∗

^aDepartment of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, India-221005, India

^bDepartment of Chemistry, Pondicherry University, Kalapet, Pondicherry, India-605014, India

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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

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References

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