Abstract Enantioselective oxidation of aliphatic C—H bonds is the most straightforward and atom-economical approach to prepare chiral oxygenated hydrocarbon skeletons, which are ubiquitous in molecules of biological and industrial relevance. In Nature, this reaction is carried out by metalloenzymes with high levels of efficiency and selectivity. Due to the exquisite performance of enzymatic systems, their active site has served as inspiration for the exploration of artificial catalysts, such as those based on porphyrins or coordination compounds with tetradentate salen- or bis-amine-bis-pyridine-type ligands. Reviewed herein are the latest advances in enantioselective C—H oxidations using biologically inspired iron and manganese complexes.