The first allylindation of norbornenol derivatives has been realised highly regio- and stereoselectively. The reactions of allylindium sesquiiodide with syn-bicyclo[2.2.1]hept-2-en-7-ol and endo-bicyclo[2.2.1]hept-5-en-2-ol gave allylated products together with iodinated and oxygenated compounds. The product distribution could be controlled by changing the reaction solvent. In these reactions, the regio- and stereochemistry of the addition of the allylindium reagent is highly regulated via the chelation with the neighbouring hydroxyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.