Metalated nitriles are highly nucleophilic, tunable nucleophiles. Much of the unique reactivity stems from the exceptionally small size of the C º N group combined with the high inductive polarization imparted by the excellent electron withdrawing effect of the nitrile group. Tuning the site of metal coordination allows the metalated nitrile to be tuned from being planar, through partially pyramidal to fully tetrahedral.

Understanding the unusual reactivity of metalated and unsaturated nitriles has led to many new synthetic methods for selectively generating new stereocenters and has led to several innovative approaches to medicinally important bicyclic carbocycles. Descriptions of this chemistry, the research group and facilities, and current projects are available on our group website.