This paper outlines the stereocontrolled synthesis of a functionalised spiropiperidine through a diastereoselective tandem RCM reaction. The diastereoselectivity of this process was found to be strongly dependant on the nature of the catalyst; the less active first generation Ru–carbene complexes provided the desired spirocycle in high yield and with good stereocontrol. Additionally, the further functionalisation of the spiropiperidine was ...