Double nucleophilic addition of trimethylsilyl cyanide to α,β-unsaturated aldimines promoted by aluminum chloride:: Preparation of 2-aminopentanedinitrile

In the presence of AlCl3, trimethylsilyl cyanide underwent 1,4- and subsequent 1,2-additions with alpha,beta-unsaturated imines to give 2-aminopentanedinitriles in good yields. An asymmetric version of this type of bis-cyanation was successfully conducted using a chiral alpha,beta-unsaturated imine possessing a phenylglycinol derivative as a chiral auxiliary.