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: lectka
jhu.edu
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
Abstract
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.
see article for more examples
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
