Stereoselective Entry to Bicyclic β-Lactams via Free Radical Cyclization of 2-Azetidinone-Tethered Bromohomoallylic Alcohols

Abstract

Triphenyltin hydride-promoted reaction of β-lactam-tethered bromodienes gave six-, seven-, or eight-membered bicyclic ring structures through intramolecular free radical cyclization. The cyclization precursors were synthesized by stereoselective tin-mediated carbonyl bromoallylation of 4-oxoazetidine-2-carbaldehydes in an aqueous environment.

Key words

carbonyl additions - cyclizations - lactams - radical reactions - tin

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