Abstract The E-configurated 3-(ω-iodoalkylidene)-piperidin-2-ones 1a-e were prepared from the corresponding ω-tert-butyldimethylsilyloxyalkanals 5a-e by aldol condensation with N- tert-butyloxycarbonylpiperidone, subsequent silyl deprotection and iodo-dehydroxylation. In the presence of tributylstannane as the reducing agent and of triethylborane as the initiator the iodides underwent a reductive radical cyclization to the corresponding products rac-9a ...