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Treatment of N-alkyl-3-sulfonyl glutarimides (1) with sodium hydride and then lithium aluminum hydride could give regioselective reduced hydroxy piperidones (5) which were further dehydrated to 3,4-dihydro-3-tosylpyridin-2-ones (6) in the presence of boron trifluoride.

γ-Substituted α,β-unsaturated δ-lactams 1 was synthesized from α-sulfinyl acetamides 3 in three steps. Formal synthesis of (±)-protoemetinol was also reported.

A formal [3+3] cycloaddition strategy to substituted glutarimides was studied. N -Benzyl α-sulfonylacetamides and various α,β-unsaturated esters were used as starting materials.