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

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

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

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.

Original language	English
Pages (from-to)	1167-1174
Number of pages	8
Journal	Synthesis (Germany)
Volume	56
Issue number	7
DOIs	https://doi.org/10.1055/a-2179-8669
State	Published - 29 Aug 2023
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2023. Thieme. All rights reserved.

Keywords

2-deoxy-aryl- C -glycosides
aryl- C -glycosides
glycal enones
glycosides
synthetic methods

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10.1055/a-2179-8669

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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.",

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AU - Kandasamy, Jeyakumar

PY - 2023/8/29

Y1 - 2023/8/29

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AB - 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.

KW - 2-deoxy-aryl- C -glycosides

KW - aryl- C -glycosides

KW - glycal enones

KW - glycosides

KW - synthetic methods

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

Abstract

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