Conversion of Amides into 2,2-Disubstituted Amines

Significance

2,2-Bis-alkylated cyclic amines are widely distributed scaffolds of natural biologically active compounds, as well as important pharmacophores. Thioiminium salts, readily available from lactams and amides, are found to be useful intermediates for the synthesis of this class of amines. Bis-allylation, -benzylation and -alkylation of thioiminium salts with organomagnesium and organocerium reagents proceeds at room temperature with high yields. Ring-closing metathesis of the diallylated products gives useful spiro compounds.