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

Ciby J. Abraham, Daniel H. Paull, Cajetan Dogo-Isonagie, Thomas Lectka*

*Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA, Email: lectkajhu.edu

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

DOI: 10.1055/s-0029-1217348

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Abstract

A catalytic, highly diastereoselective synthesis of trans-β-lactams is based on a phosphonium fluoride precatalyst that both activates the nucleophile and directs the reaction process for high yield and diastereoselectivity.

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

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

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Key Words

β-lactams, diastereoselectivity, cycloaddition, organocatalysis, imine, ketene acetal, phosphonium fluoride precatalyst

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ID: J60-Y2009-1840