One-pot silyl ketene imine formation-nucleophilic addition reactions of acetonitrile with acetals and nitrones

Grace Ann Robertson

Acetonitrile is converted to a mildly nucleophilic silyl ketene imine (SKI) by trimethylsilyl trifluoromethanesulfonate (TMSOTf) and Hunig's base in situ. Acetal and nitrone electrophiles are activated by TMSOTf acting as a Lewis acid catalyst. The activated acetals and nitrones then react with the SKI to form the product β-methoxynitriles and β-(silyloxy)aminonitriles, respectively. The entire reaction occurs in a single reaction vessel, improving efficiency of the cyano-functional group addition.




Wade Downey