Copper-Catalyzed Intermolecular Generation of Ammonium Ylides with Subsequent [2,3]Sigmatropic Rearrangement. Efficient Synthesis of Bifunctional Homoallylamines

The [2,3]sigmatropic rearrangement of allylic ammonium ylides generated by the reaction of N,N-dimethyl-1-alkyl-2-methylallylamines derived from terpene alcohols with diazo compounds in the presence of copper catalysts gave trisubstituted E-olefins in one-pot. In addition, a cyano substituent at the 2-position of N,N-dimethylallylamine increased the occurrence of the catalytic [2,3]sigmatropic rearrangement to give the corresponding bifunctional homoallylamines.