Stereoselective Syntheses of Allylic Amines Through Reduction of 1-Azadiene Intermediates

Abstract The stereoselective synthesis of primary and secondary E -allylic amines by reduction of 1-azadiene intermediates is described. β-Enamino phosphonium salts are suitable starting materials to prepare secondary allylic amines. Two methods are reported for the obtention of primary allylic amines from 4-amino-1-aza-1,3-dienes. Method A leads to the desired compounds by straight reduction with AlH 3 or DIBALH; method B is a stepwise procedure that allows for better yields when sterically hindered 4-amino-1-aza-1,3-dienes are employed.