Synthetic application of in situ generation of N-acyliminium ions from α-amido p-tolylsulfones for the synthesis of α-amino nitriles

In the presence of catalytic amount of bismuth bromide (5 mol%) the alpha-amido p-tolylsulfones are converted into N-acyliminium ions, which undergo the nucleophilic addition of trimethylsilyl cyanide (TMSCN) to provide the N-protected alpha-amino nitriles in very good yield A variety of alpha-amido p-tolylsulfones were prepared from aromatic as well as aliphatic aldehydes for the synthesis of alpha-amino nitriles (C) 2010 Elsevier Ltd. All rights reserved