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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, Email: norbert.dekimpeUGent.be

W. Van Brabandt, M. Vanwalleghem, M. D'hooghe, N. De Kimpe, J. Org. Chem., 2006, 71, 7083-7086.

DOI: 10.1021/jo0608319 (free Supporting Information)


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Abstract

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.


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Key Words

Staudinger Synthesis, Acetonides, Sodium Periodate, Imines, Sodium Borohydride, N-Heterocycles


ID: J42-Y2006-2740