Stereodivergent allylindation of cyclopropene derivatives has been realised regio- and stereoselectively. The coupling occurs exclusively at the gamma-carbon of allylic indium reagents and the more substituted carbon of the cyclopropene double bond The carboxyl and hydroxymethyl groups on the cyclopropene C-3-carbon exert significant effects in cis-direction and acceleration of the allylindation based on the intramolecular chelation, whereas the ester group directs a trans-addition owing to the steric interaction with incoming allylindium reagents. (C) 1998 Elsevier Science Ltd. All rights reserved.