Selective oxidation of terpenes is a key enabling route to produce value-added epoxides from renewable raw materials. In the present work, the photo-assisted oxygen atom transfer (OAT) to renewable monoterpenes, such as a-pinene, beta-pinene, camphene, (R)-(+)-limonene and (S)-(-)-limonene was evaluated with a dichloro-dioxoBipy molybdenum((VI)) complex (Bipy = 2,2' -bipyridine-4,4'-dicarboxylato) anchored on TiO2 nanotubes (labeled as Mo((VI))Cl(2)O(2)Bipy/TiO2-NT) using molecular oxygen as a primary oxidant under benign ambient conditions. Supported MoO3 on TiO2 nanotubes were also used for comparison purposes. Photooxidation of a-pinene with that MoO3/TiO2-NT catalyst resulted in a low conversion and in products distribution similar to that of the parent titania nanotubes, with the ketone as the main product due to a radical process. In contrast, all monoterpenes were successfully oxidized by the Mo((VI))Cl(2)O(2)Bipy/TiO2-NT catalyst to the desired epoxides with high selectivities due to the OAT with O-2 and UV-vis light. Additionally, the photo-stimulated OAT to (R)-(+)and (S)-(-)-limonene with the immobilized dioxo-Mo-(VI) complex resulted in a diastereomeric excess (d.e.) for the cis-limonene-1,2-epoxide isomers relative to the trans isomers (d.e. = 36 and 34 %, respectively), thereby suggesting that the chiral center in the (R)-(+)- and (S)-(-)-limonene governs the formation of the diastereoisomer. Although not chiral, the Mo((VI))Cl(2)O(2)Bipy/TiO2-NT catalyst was shown to act stereoselectively during the OAT process. The high stability of the Mo((VI))Cl(2)O(2)Bipy -catalyst under the reaction conditions was also ascertained by recycling studies.