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Synfacts 2006(4): 0323-0323  
DOI: 10.1055/s-2006-932074
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Phosphono-β-Lactams

Contributor(s): Victor Snieckus, Robert Engqvist
K. Moonen, C. V. Stevens*
Ghent University, Belgium
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

The synthesis of phosphono-β-lactams starting from combination of imines with α-chloroacetyl chloride is reported. The initially formed N-acetylated imminium salts, upon treatment with trialkyl phosphites, undergo a Micha­elis-Arbuzov-type reaction to afford adducts which, upon cyclization under NaH conditions, furnish the 4-phosphono-β-lactams in good to excellent yields.