Asymmetric synthesis of 1-(2- and 3-haloalkyl)azetidin-2-ones as precursors for novel piperazine, morpholine, and 1,4-diazepane annulated beta-lactams.
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 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.
Van Brabandt
Willem
W
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium.
Vanwalleghem
Matthieu
M
D'hooghe
Matthias
M
De Kimpe
Norbert
N
D001384:Azetidines / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry*; D000077489:Piperazine; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry*; D047090:beta-Lactams / Q000138:chemical synthesis / Q000737:chemistry*
D001384:Azetidines; D009025:Morpholines; D010879:Piperazines; D047090:beta-Lactams; D000077489:Piperazine; C037574:morpholine