Journal of Organic Chemistry 2013-09-20

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

Benito Alcaide, Pedro Almendros, Teresa Martínez del Campo, M Rosario Torres

Index: J. Org. Chem. 78(18) , 8956-65, (2013)

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Abstract

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.