The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction

A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2,3- and 2,4disubstituted cyclopentanones. The Stetter reaction of 2,5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis-diasteroiners with low ee. (c) 2005 Elsevier Ltd. All rights reserved.