A Facile Highly Regio- and Stereoselective Preparation of N-Tosyl Allylic Amines from Allylic Alcohols and Tosyl Isocyanate via Palladium(II)-Catalyzed Aminopalladation−β-Heteroatom Elimination

The high regio- and stereoselectivity have been obtained from the allylic substitution reaction catalyzed by palladium(II) species. From allylic alcohols, one-pot reaction with tosyl isocyanate followed by palladium(II)-catalyzed allylic substitution gives N-tosyl (E)-allylic amines in high yield. The substitution occurs only at the gamma-position of the 1- or 3-substituted allylic alcohols.