Gold(I)-Catalyzed Access to 1-Alkynyl <i>C</i>-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 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.
Authors
- Catherine Taillier (ORCID: https://orcid.org/0000-0001-9277-0130)
- Vincent Dalla (ORCID: https://orcid.org/0000-0001-9043-5996)
- Patrick Pale (ORCID: https://orcid.org/0000-0002-3924-530X)
- Eliot Starck
- Aurélien Blanc (ORCID: https://orcid.org/0000-0003-4240-3281)
- Jean‐Marc Weibel (ORCID: https://orcid.org/0000-0002-4473-2073)
- Mathieu Pascaretti
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université Le Havre Normandie (FR)
- Normandie Université (FR)
- Institut de Chimie (FR)
- Unité de Recherche en Chimie Organique et Macromoléculaire (FR)
- Université de Strasbourg (FR)
Publication Details
- Journal
- ACS Catalysis
- Published
- 2024-09-23
- DOI
- https://doi.org/10.1021/acscatal.4c04293
- Citations
- 2
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Université de Strasbourg
- Ministère de l'Education Nationale, de l'Enseignement Superieur et de la Recherche
- Centre National de la Recherche Scientifique
- Conseil régional du Grand Est
- Région Normandie