Silver-Catalyzed Desymmetrization via Carbon Dioxide Incorporation

Significance

Alkylidene cyclic carbonates are important intermediates in organic synthesis. Much effort has been invested into the reaction of carbon dioxide with propargyl alcohols as a ‘green’ method for their synthesis. This area still remains challenging as often high pressures and harsh conditions are required for the incorporation of carbon dioxide. Previously, the authors reported mild conditions for the formation of alkylidene cyclic carbonates from carbon dioxide and propargyl alcohols in the presence of a catalytic amount of silver salt and base (W. Yamada et al. Eur. J. Org. Chem. 2007, 2604). In the present communication the authors report the enantio­selective synthesis of alkylidene cyclic carbonates by silver-catalyzed desymmetrization of propargyl alcohols in excellent yield and selectivity.