Gold(I)-Catalyzed Reactions of <i>exo</i>-Glycals with Propargyl Esters toward C-1 Alkenyl Spirocyclopropyl Carbohydrates
An atom-economic and diazo-free strategy for the construction of novel pseudo anomeric C-1 alkenyl spirocyclopropyl sugars is described. Leveraging the 1,2-migration pathway of propargyl esters under gold(I) catalysis, easily available <i>exo</i>-glycals undergo β-selective alkenylcarbenoid insertion in moderate to excellent yields. Preferential activation of propargyl moieties and concerted [2 + 1] insertion are both favored through ligand choice and electron enrichment of esters. Stereocontrol using conformational bias and rearrangement are also demonstrated.
Authors
- Delphine Hatey
- Aurélien Blanc (ORCID: https://orcid.org/0000-0003-4240-3281)
- Philippe Compain (ORCID: https://orcid.org/0000-0002-6877-0859)
- Mylène Lang (ORCID: https://orcid.org/0000-0001-7323-6514)
- Nicolas Kern (ORCID: https://orcid.org/0000-0002-8825-1669)
- S. Walter
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université de Haute-Alsace (FR)
- Institut de Chimie (FR)
- Université de Strasbourg (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-16
- DOI
- https://doi.org/10.1021/acs.orglett.4c02754
- Citations
- 5
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- Université de Strasbourg
- Centre National de la Recherche Scientifique
- Ministère de l'Enseignement supérieur, de la Recherche et de l'Innovation