Asymmetric synthesis of 1-(2- and 3-haloalkyl)azetidin-2-ones as precursors for novel piperazine, morpholine, and 1,4-diazepane annulated beta-lactams

被引：38
作者：
Van Brabandt, Willem [1 ]
Vanwalleghem, Matthieu [1 ]
D'hooghe, Matthias [1 ]
De Kimpe, Norbert [1 ]
机构：
[1] Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 18期
关键词：
D O I：
10.1021/jo0608319
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A high-yielding, asymmetric synthesis of novel 4-formyl1-(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, beta-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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收藏
页码：7083 / 7086
页数：4
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