N-Heterocyclic Carbene-Catalyzed [4+2] Annulation of Acetates and β-Silyl Enones: Highly Enantioselective Synthesis of β-Silyl δ-Lactones

Asymmetric synthesis of chiral organosilanes with a potential application was realized by N-heterocyclic carbene-catalyzed [4+2] annulation of acetates and beta-silyl enones. This strategy exhibits easy to obtain raw materials, mild reaction conditions, good substrate tolerance, simple operation and so on. Notably, excellent yield and enantioselectivity were also observed with expanding the reaction scale by 10 times. The target product showed excellent results in hydrogenation reduction. Moreover, the hypolipidemic drug ezetimibe was obtained through the synthetic transformation of the resulting products.

Automated summary

The asymmetric synthesis of chiral organosilanes was achieved through a novel synthetic strategy, showing promising results and potential applications in the future.