The hydrogenation of (S)-proline-modified anthranilic acid was studied on Rh and Ru catalysts. The hydrogenation occurred with a very high diastereoselectivity but a moderate chemoselectivity. In general, the carbon-supported catalysts exhibited a higher activity but a lower diastereoselectivity than the alumina-supported catalysts. The use of water as the solvent instead of ethanol resulted in higher activities but lower diastereoselectivities. Rh- and Ru-based homogeneous catalysts gave a comparable selectivity but a lower activity than their heterogeneous counterparts.