Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru (η3-methallyl) 2 (cod) and a trans-chelating chiral bisphosphine ligand, PhTRAP. This is the first successful catalytic asymmetric reduction of 5-membered ...