The preparation of 2-triazolyl-and 2-tri-A C H T U N G T R E N N U N G azolylmethylpyrrolidines from l-proline and l-trans-4-hydroxyproline is described, along with their evaluation as chiral ligands in ruthenium-catalyzed asymmetric transfer hydrogenation. Modular evolution of the ligands by introduction of remote substituents is also presented, showing a surprisingly important effect on the performance of the ligands.