Phosphine-catalyzed fixation of CO2 with γ-hydroxyl alkynone under ambient temperature and pressure: kinetic resolution and further conversion

Abstract

Multiple skeleton derived γ-hydroxyl alkynones could be activated by phosphine, which then underwent cycloaddition with CO₂ to afford functionalized carbonate products under ambient temperature and pressure. These functionalized carbonate products could easily release CO₂ under heating conditions, giving a diversity of furanones in excellent yields. The optically active functionalized cyclic carbonates could be afforded through the kinetic resolution of propargyl alcohols via carbon dioxide fixation catalyzed by a new series of sterically hindered and highly nucleophilic bifunctional amino acid-derived phosphine catalysts with moderate to excellent selectivities. Plausible mechanisms were proposed and supported by isotope-labeling experiments and DFT calculations.