Work

Gold(I)-Catalyzed Reactions of exo-Glycals with Propargyl Esters toward C-1 Alkenyl Spirocyclopropyl Carbohydrates

Year: 2024

Type: article

Abstract: 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 exo -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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c02754

Authors: Mylène Lang, Sophie Walter, Delphine Hatey, Aurélien Blanc, Philippe Compain, Nicolas Kern