Stereoretentive Conversion to C-Glycosides from S-Glycosides via Ligand-Coupling on Sulfur(IV)

Organic Letters, Год журнала: 2025, Номер 27(4), С. 954 - 960

Опубликована: Янв. 21, 2025

A novel strategy is reported for the stereoselective synthesis of C(sp2)-C(sp3) C-glycosides, which converts heteroaryl S-glycosides into C-glycosides with retention configuration through a sequential process involving oxidation and Grignard reagent attack. The new method involves generation S(IV) intermediate, followed by ligand coupling glycosyl groups to yield C-glycosides. diverse were achieved good efficiency.

Язык: Английский

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Insertion of Glycosylidene Carbenes into Phenolic O–H Bonds for the Synthesis of O-Aryl Glycosides

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 18, 2025

We present a new strategy for the synthesis of O-aryl glycosides through formal insertion glycosylidene carbenes into O–H bond phenols. The key carbene intermediates were generated in situ by copper-catalyzed oxidation bench-stable diaziridine precursors. This method enables glycosylation variety phenols with good yields, excellent diastereoselectivity, and chemoselectivity, providing highly practical late-stage complex natural products bioactive agents.

Язык: Английский

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Taming glycosylidene carbenes through bench-stable glycosylidene diaziridines to access boro-ketosides

Chem Catalysis, Год журнала: 2024, Номер 4(4), С. 100980 - 100980

Опубликована: Апрель 1, 2024

Язык: Английский

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