A hydrophilic chiral diamine from d-glucose in the Rh(I) catalysed asymmetric hydrogenation of acetophenone

A strategy for the synthesis of a new hydrophilic chiral diamine derived from α-d-glucose is described. The compound is obtained by introducing proper nitrogen functions at C2 and C3 positions of the sugar ring, and by deprotecting positions 4 and 6. The efficiency of the ligand in the Rh(I)-catalysed hydrogenation of acetophenone has been examined by using isopropanol and ethanol as hydrogen sources. The secondary alcohol has been obtained in ees up to 50%.