Synthesis of fused-β-lactams through selective gold-catalyzed oxycyclization of dioxolane-tethered enynes

摘要

The gold-catalyzed preparation of 2-azetidinone-fused oxacycles was accomplished from β-lactam-linked enynes through heterocyclization reaction taking advantage of the acetonide pendant group. While the synthesis of fused tetrahydrofuran-β-lactams from 1,3-enynes could be considered as an unusual metal-catalyzed cyclization of enynols, α-alkoxy dioxolane-tethered 1,3-enynes exclusively undergo bis-oxycyclization to afford tricyclic bridged acetals. © 2013 American Chemical Society.