Oxidative Kinetic Resolution-Claisen Rearrangement Sequence to Enantioenriched Arylcycloalkenes, David C. Ebner, Zoltán Novák, Brian M. Stoltz, Synlett 2006, 20, 3533-3539. DOI: 10.1055/s-2006-958415 | [Full Text Link]
The Pd-catalyzed oxidative kinetic resolution of secondary alcohols afforded enantioenriched allylic alcohols with high selectivity. These alcohols were transformed into arylcycloalkenes with enantioenriched tertiary and quaternary stereocenters through a two-step vinylation and Lewis acid promoted Claisen rearrangement. Subsequent Pd-catalyzed oxidative cyclization of a Claisen product afforded a 5,5-fused tetrahydrofuran.