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 α-amido p-tolylsulfones are converted into N-acyliminium ions, which undergo the nucleophilic addition of trimethylsilyl cyanide (TMSCN) to provide the N-protected α-amino nitriles in very good yield. A variety of α-amido p-tolylsulfones were prepared from aromatic as well as aliphatic aldehydes for the synthesis of α-amino nitriles.

Graphical abstractThe α-amido p-tolylsulfones derived from aromatic and aliphatic aldehydes react with TMSCN in the presence of BiBr3 (5 mol %) as catalyst to give the N-protected α-amino nitriles in very good yield.Download full-size image