METAL-MEDIATED 2-ATOM CARBOCYCLE ENLARGEMENT IN AQUEOUS-MEDIUM

The indium and tin-mediated carbonyl allylations of 1,3-dicarbonyl com pounds have been studied in aqueous medium. The study led to the devel opment of a novel two-atom carbocycle-enlargement in water. Five-, six -, seven-, eight-, and twelve-membered rings are enlarged by two carbo n atoms into seven-, eight-, nine-, ten-, and fourteen-membered ring d erivatives respectively. Tetralone derivatives are similarly expanded to 6-8 fused ring systems; and indanone derivatives are expanded to 5- 7 fused ring systems. The use of both indium and zinc as the metal med iators provided the ring expansion products successfully. The use of w ater ar a solvent was found to be essential for the ring expansion rea ction. (C) 1998 Elsevier Science Ltd. All rights reserved.