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Synthesis 2005(2): 193-198  
DOI: 10.1055/s-2004-831248
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Halogen-Lithium Exchange Reaction of 3,3-Dichloro-2-azetidinones: Application to the Synthesis of cis-4-Aryl-3-chloro-2-azetidinones

Yves Dejaegher, Bram Denolf, Christian V. Stevens, Norbert De Kimpe*
Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
Fax: +32(9)2646243; e-Mail: Norbert.dekimpe@UGent.be;
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Publication History

Received 13 February 2004
Publication Date:
11 January 2005 (online)

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Abstract

A straightforward synthesis of new cis-4-aryl-3-chloro-2-azetidinones was developed, using a halogen-lithium exchange reaction on 4-aryl-3,3-dichloro-2-azetidinones. This methodology was further extended to the use of alkyl halides as electrophiles, while more complex electrophiles could not be introduced.

Key words

lactams - lithiation - stereoselectivity - alkylations - azetidinones