Gold(I)-Catalyzed Access to 1‑Alkynyl C‑Glycosides from 1‑Silylated Alkynes: An Alternative Paradigm for the Direct and α‑Stereoselective Alkynylation of Glycosides

Gold(I)-Catalyzed Access to 1‑Alkynyl C‑Glycosides from 1‑Silylated Alkynes: An Alternative Paradigm for the Direct and α‑Stereoselective Alkynylation of Glycosides

Analogous to O-glycosides, C-glycosides are natural products exhibiting various bioactivities. Alkynyl C-glycosides represent important key intermediates toward more complex derivatives; however, a convenient access through a single catalytic and highly stereocontrolled step remains an important and...

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Veröffentlicht in:ACS catalysis 2024-10, Vol.14 (19), p.14863-14870
Hauptverfasser: Starck, Eliot, Pascaretti, Mathieu, Taillier, Catherine, Blanc, Aurélien, Dalla, Vincent, Pale, Patrick, Weibel, Jean-Marc
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container_end_page 14870
container_issue 19
container_start_page 14863
container_title ACS catalysis
container_volume 14
creator Starck, Eliot
Pascaretti, Mathieu
Taillier, Catherine
Blanc, Aurélien
Dalla, Vincent
Pale, Patrick
Weibel, Jean-Marc
description Analogous to O-glycosides, C-glycosides are natural products exhibiting various bioactivities. Alkynyl C-glycosides represent important key intermediates toward more complex derivatives; however, a convenient access through a single catalytic and highly stereocontrolled step remains an important and only partially solved challenge. Here, a mechanistically designed gold­(I)-catalyzed silyl-assisted efficient and highly α-stereoselective process is reported. The postulated mechanism has been ascertained by combining 1H, 31P and VT NMR and in situ MS experiments.
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title Gold(I)-Catalyzed Access to 1‑Alkynyl C‑Glycosides from 1‑Silylated Alkynes: An Alternative Paradigm for the Direct and α‑Stereoselective Alkynylation of Glycosides
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