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Communication | Special issue | Vol 76, No. 1, 2008, pp.203-208
Published online, 28th April, 2008
DOI: 10.3987/COM-08-S(N)43
Regioselective Double Nucleophilic Addition Reaction Leading to the Synthesis of β-Lactams

Atsushi Takahashi, Shiho Kawai, Iwao Hachiya, and Makoto Shimizu*

*Department of Chemistry for Materials, Graduate School of Engineering Mie University, Tsu, Mie 514-8507, Japan

Abstract

β-Lactams were prepared in a regio- and stereoselective manner using the double nucleophilic addition of ketene silyl acetals and ketene silyl thioacetals to α,β-unsaturated imines followed by base-promoted cyclization. An attempted approach to 2-aryl carbapenem is also described.