Efforts were made at obtaining good enantioselectivities in the epoxidation of simple olefins using methyltrioxorhenium(VII) (MTO) catalyst, urea-hydrogen peroxide (UHP) and six different chiral non-racemic 2-substituted pyridine ligands (four of which are completely novel). UHP was chosen as the hydrogen peroxide source to avoid unfavorable competition from water for vacant sites on the metal. The ligands were chosen because of putative formation of stable 5- and 6-membered chelates with the metal centre. All were synthesised in an efficient manner. Enantioselective epoxidations took place (3-12% cc) with some very good conversions. (c) 2005 Elsevier B.V. All rights reserved.