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Readily available 4-formyloxyazetidinone was enantioselectively transformed into 4-substituted azetidinones upon treatment with 0.1 equiv. of the cinchona alkaloid (quinidine) in toluene via intermolecular nucleophilic trapping of the N-acylimine intermediate by mercapto-, or hydroxymoieties of thiophenols, thiols, phenols and alcohols. Additionally, biological activity tests were performed on the newly synthesized β-lactams.

Quinidine catalyzed reaction between 4-formyloxy-azetidin-2-one and some thiophenols, thiols and alcohols