Abstract The stereoselective oxidation of differently functionalised benzyl phenyl sulfides has been examined by using enantiopure Ti IV trialkanolamine complexes. These complexes efficiently catalyse the sulfoxidation with good stereoselectivities. The data highlight the contribution to the stereoselectivity of steric effects and non-covalent π–π interactions between the aromatic rings of the Ti IV complex and those pertaining to the ...