Synthesis of Chiral Homoallylic Nitriles by Iridium-Catalyzed Allylation of Cyanoacetates.

A synthesis of chiral homoallylic nitriles by the iridium-catalyzed allylation of cyanoacetates followed by Krapcho demethoxycarbonylation has been developed. A wide range of homoallylic nitriles were obtained with a high enantioselectivity (>95-99% ee). These compounds are useful chiral building blocks because further synthetic elaboration starting from a nitrile or terminal alkene is possible.