A novel synthetic intermediate in β-lactam chemistry: an efficient preparation of cis-1,3,4-tris(trimethylsilyl)azetidin-2-one and its transformation into 4-acetoxy-3-alkylideneazetidin-2-ones
Abstract
The addition of trimethylsilyl azide to cis-2,3- bis(trimethylsilyl)cyclopropan-1-one in the presence of a sodium azide/15-crown-5 catalyst gave cis-1,3,4-tris(trimethylsilyl)azetidin-2-one, which could easily be transformed into 4-acetoxy-3-alkylideneazetidin-2-ones by way of Peterson olefination followed by anodic oxidation.