Abstract: A totally controlled regiodivergent azidation of activated N-allenamides is presented. Using TMSN3/TBAF, β-azidation of N-allenamides occurs exclusively, yielding vinyl azides. Conversely, employing a TFA/TMSN3 mixture results solely in the formation of γ-azides. A subsequent formal Winstein rearrangement of the latter with DBU produces α-amido vinyl azides. Additionally,...[En savoir plus]
Tweet: The IFM team in collaboration with researchers at ENS Lyon and Institut Pasteur used advanced molecular simulations to investigate how cannabinoids bind to glycine receptors, an important pharmacological target for chronic pain. They discovered that tetrahydrocannabinol (THC) and anandamide (AEA) bind to more than one region of the receptor's transmembrane domain and characterized their...[En savoir plus]
Abstract: Several copper-ligands, including 1,10-phenanthroline (Phen), have been investigated for anticancer purposes based on their capacity to bind excess copper (Cu) in cancer tissues and form redox active complexes able to catalyse the formation of reactive oxygen species (ROS), ultimately leading to oxidative stress and cell death. Glutathione (GSH) is a critical compound as it is highly...[En savoir plus]
Abstract: When aiming at the direct use of CO2 for the preparation of advanced/value-added materials, the synthesis of CO2/olefin copolymers is very appealing but challenging. The δ-lactone 3-ethylidene-6-vinyltetrahydro-2H-pyran-2-one (EVP), synthesized by telomerization of CO2 with 1,3-butadiene, is a promising monomer. However, its chemoselective ring-opening polymerization (ROP) is hampered...[En savoir plus]
Abstract: The aromatic Cope rearrangement is an elusive transformation that has been the subject of a limited number of investigations compared to those seemingly close analogues, namely the Cope and aromatic Claisen rearrangement. Herein we report our investigations inspired by moderate success observed in the course of pioneering works. By careful experimental and theoretical investigations,...[En savoir plus]
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...[En savoir plus]
Abstract: 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...[En savoir plus]