Mild Protocol for the Synthesis of syn-1,2-Aminonitriles

Significance

The traditional alkylation of imines with benzylnitriles is difficult due to easy epimerization or elimination under basic conditions. The reported protocol uses a Pd(II)-pincer complex that activates the nitriles so that deprotonation can occur under unusually mild conditions for this reaction. Thus, a wide range of sulfonylimines 2 can be alkylated with ortho-substituted benzylic nitriles 1. Importantly, preliminary results show that the catalytic process may be rendered enantio­selective though the diastereoselectivity is still modest.