A simple route to side-chain fluorinated <script type="math/tex">\beta</script>-lactams from ring-fluorinated aziridines

Konev, Alexander S.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Abbaspour Tehrani, Kourosch

doi:10.1016/J.JFLUCHEM.2006.10.013

Title

A simple route to side-chain fluorinated $\beta$ -lactams from ring-fluorinated aziridines

Author

Konev, Alexander S.

Novikov, Mikhail S.

Khlebnikov, Alexander F.

Abbaspour Tehrani, Kourosch

Abstract

beta-Lactams bearing a Ph2CF substituent at the C(4)-atorn were synthesized from N-alkyl-2-fluoro-3,3-diphenylaziridines. The transformation was realized using SbF3-mediated isomerization of the monofluoroaziridines to fluorinated aldimines, followed by Staudinger reaction with ketenes. It was shown that this reaction sequence can be performed as a one-pot procedure. (c) 2006 Elsevier B.V. All rights reserved.

Language

English

Source (journal)

Journal of fluorine chemistry. - Lausanne

Publication

Lausanne : 2007

ISSN

0022-1139

DOI

10.1016/J.JFLUCHEM.2006.10.013

Volume/pages

128 :2 (2007) , p. 114-119