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Stereodivergent C-(Hetero)Aryl Glycosylation by Nickel-Catalyzed Redox-Neutral Cross-Coupling of Glycosyl Sulfonyl Hydrazides
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DOI：10.1002/anie.9453527.png)
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Abstract
En 中文
Unprotected C-aryl glycosides are ubiquitous in biologically active compounds and are widely used in chemical biology. The stereochemistry at the anomeric carbon of a C-glycoside often dictates its function. Despite past advances in C-glycosylation, methods that provide selective access to both α and β anomers are scarce due to the challenge of controlling stereoselectivity. Herein, we demonstrate that native sugars, when transformed into glycosyl sulfonyl hydrazide precursors, undergo efficient radical cross-coupling with (hetero)aryl halides under redox-neutral nickel catalysis. The method has broad scope and excellent functional group tolerance, enabling the stereodivergent synthesis of diverse C-(hetero)aryl glycosides in either α or β anomeric forms through ligand control.
Keywords:
C-(hetero)aryl glycosides
cross-coupling
glycosyl sulfonyl hydrazides
nickel catalysis
stereodivergence
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