Enantioselective Au(I)-Catalyzed Cycloisomerization/Addition of Oxygen Nucleophiles to 2-Alkynylenones by the Tethered Counterion-Directed Catalysis Strategy

The tethered counterion-directed catalysis (TCDC) strategy enables the Au(I)-catalyzed highly enantioselective synthesis of bicyclic furan derivatives via a reaction sequence combining the cycloisomerization of 2-alkynyl enones and the addition of nucleophiles. A large range of oxygenated nucleophiles, such as water, alcohols, carboxylic acids, and peroxides, have successfully been used as nucleophiles, delivering the chiral furane derivatives in high enantioselectivities (mostly above 90% enantiomeric excess). The CPAphosAuCl complexes were used with catalytic loadings as low as 0.2 mol % in most cases, in combination with silver carbonate as the chloride abstractor.