N-Heterocyclic Carbene-Catalyzed Ireland–Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones

Abstract

The N-heterocyclic carbene (NHC)-catalyzed Claisen rearrangement of hybrid Ireland-Coates structures has been achieved, allowing the stereoselective synthesis of highly functionalized β-lactones. The reaction proceeds with high diastereoselectivity (>20:1) and affords a diverse range of β-lactone fused cyclopentanes. Mechanistic studies are detailed.