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The Development of the First Catalyzed Reaction of Ketenes and Imines: Catalytic, Asymmetric Synthesis of β-Lactams

Andrew E. Taggi, Ahmed M. Hafez, Harald Wack, Brandon Young, Dana Ferraris and Thomas Lectka*

*Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, Email:

A. E. Taggi, A. M. Hafez, H. Wack, B. Young, D. Ferraris, T. Lectka, J. Am. Chem. Soc., 2002, 124, 6626-6635.

DOI: 10.1021/ja0258226


A practical methodology for the catalytic, asymmetric synthesis of β-lactams results from the development of a catalyzed reaction of ketenes (or their derived zwitterionic enolates) and imines using benzoylquinine as chiral catalyst and proton sponge as the stoichiometric base.

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reaction pathway

Diastereoselective Synthesis of trans-β-Lactams Using a Simple Multifunctional Catalyst

C. J. Abraham, D. H. Paull, C. Dogo-Isonagie, T. Lectka, Synlett, 2009, 1651-1654.

Key Words

Staudinger Synthesis, β-Lactams, Organocatalysis

ID: J48-Y2002-1730