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Racemic as well as optically pure fused tricyclic β-lactams are regio and stereoselectively prepared via intramolecular nitrile oxide-alkene cycloaddition reaction of 2-azetidinone-tethered alkenyl oximes or nitro alkanes. The process is more efficient when the nitrile oxide moiety is separated by a methylenic group, rather than being directly linked to the C-4 position of the four- membered ring.

Intramolecular 1,3-dipolar cycloaddition reaction of novel 2-azetidinone-tethered alkenyl nitrile oxides