Enantioselective synthesis of bicarbocyclic structures with an all-carbon quaternary stereocenter through sequential cross metathesis and intramolecular Rauhut-Currier reaction

A new extension of the Birch-Cope sequence is described which allows the efficient enantioselective construction of highly functionalized, fused bicarbocyclic structures with an all-carbon quaternary stereo-center in two steps. The two-step sequence includes a cross metathesis between a terminal alkene and a polarized alkene followed by an intramolecular Rauhut-Currier reaction with a trialkylphosphine catalyst. (C) 2010 Elsevier Ltd. All rights reserved.