Enantioselective Synthesis of Functionalized beta-Lactones by NHC-Catalyzed Aldol Lactonization of Ketoacids

摘要

N-Heterocyclic carbene (NHC)-catalyzed intramolecular aldol lactonization of readily available ketoacids leading to the enantioselective synthesis of cyclopentane-fused beta-lactones is presented. The reaction proceeds via the generation of NHC-bound enolate intermediates formed from the ketoacids in the presence of the peptide coupling reagent HATU and NHC generated from the chiral triazolium salt. The functionalized beta-lactones are formed under mild conditions in high yields and enantioselectivities.