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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

2006; American Chemical Society; Volume: 71; Issue: 18 Linguagem: Inglês

10.1021/jo0608319

1520-6904

Willem Van Brabandt, Matthieu Vanwalleghem, Matthias D'hoogh, Norbert De Kimpe,

Synthesis and Biological Activity

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.