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A new type of reagent, γ-methylidene-δ-valerolactones, has been devised, which acts as a four-carbon unit in a Pd-catalyzed cycloaddition reaction through the formation of a 1,4-zwitterionic species. The utility has been demonstrated in the context of stereoselective [4+3] cycloaddition with nitrones to provide highly functionalized 1,2-oxazepines, including the asymmetric variant with high enantioselectivity.

γ-Methylidene-δ-valerolactones as a coupling partner for cycloaddition: Palladium-catalyzed [4+3] cycloaddition with nitrones