N-Trimethylsilyl Imines: Applications to the Synthesis of β-Lactams

Article abstract of DOI:10.1021/ja00329a029

Ester enolates and N-trimethylsilyl imines react to afford N-protio-β-lactams.The stereochemical course of the reaction depends on the ester enolate geometry.Therefore (E)-enolates give mainly cis β-lactams while (Z)-enolates give nearly equal mixtures of cis and trans β-lactams.The use of ethyl β-hydroxybutyrate as the ester component allows the preparation of β-lactams of potential use in carbapenem synthesis.The differences in the behavior of N-trimethylsilyl and N-aryl imines in ester-imine condensations are also discussed.