The Dynamic Kinetic Resolution of Azlactones with Thiol Nucleophiles Catalyzed by Arylated, Deoxygenated Cinchona Alkaloids

Abstract

A significant improvement of the available organocatalytic methods (in terms of product substrate scope and product enantiomeric excess) for the generation of enantioenriched α-amino acid thioesters via the dynamic kinetic resolution of azlactones is reported. C-9 arylated cinchona alkaloid catalysts have been found to be considerably superior to other bifunctional alkaloid catalysts as the promoters of this asymmetric process.