Synthesis 2005(20): 3603-3612  
DOI: 10.1055/s-2005-918440
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of N-Chloroacetyl 1-Aminoalkyl Phosphonates - Precursors of 4-Phosphono-β-Lactams

Kristof Moonen, Christian V. Stevens*
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, 9000 Gent, Belgium
Fax: +32(9)2646243; e-Mail: chris.stevens@UGent.be;
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Publikationsverlauf

Received 13 June 2005
Publikationsdatum:
27. Oktober 2005 (eFirst)

Abstract

4-Phosphono-β-lactams are synthesized via a three-step sequence, including final formation of the C3-C4 bond through a phosphorus-stabilized carbanion. The chlorinated precursors can be synthesized via two different methods: a one-pot N-acylation of an aromatic imine followed by addition of a trialkyl phosphite or phosphonylation of a suitable imine followed by N-acylation in a separate reaction step. The former method was preferred because of the ease of the reaction and the good yields obtained.

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