Asymmetric Synthesis of 1-(2- and 3-Haloalkyl)azetidin-2-ones as Precursors for Novel Piperazine, Morpholine, and 1,4-Diazepane Annulated Beta-Lactams

Willem Van Brabandt, Matthieu Vanwalleghem, Matthias D'hooghe, and Norbert De Kimpe*
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium norbert.dekimpe@UGent.be
J. Org. Chem., 2006, 71 (18), pp 7083–7086
DOI: 10.1021/jo0608319
Publication Date (Web): August 3, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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A high-yielding, asymmetric synthesis of novel 4-formyl-1-(2- and 3-haloalkyl)azetidin-2-ones was developed as valuable starting materials for the synthesis of different enantiomerically enriched bicyclic azetidin-2-ones, such as piperazine, morpholine, and 1,4-diazepane annulated β-lactam derivatives. Especially the hydride reduction of 4-imidoyl-1-(2- and 3-haloalkyl)azetidin-2-ones turned out to be an efficient and straightforward method for the preparation 2-substituted piperazines and 1,4-diazepanes.

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History

  • Published In Issue September 01, 2006
  • Received April 20, 2006

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