Stereoselective syntheses of allylic amines through reduction of 1-azadiene intermediates

The stereoselective synthesis of primary and secondary E-allylic amines by reduction of 1-azadiene intermediates is described. beta-Enamino phosphoniu m 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 strai ght reduction with AlH3 or DIBALH; method B is a stepwise procedure that al lows for better yields when sterically hindered 4-amino-1-aza-1,3-dienes ar e employed. (C) 2000 Elsevier Science Ltd. All rights reserved.