Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 2061-2071
doi:10.1351/pac200577122061
New reactions of functionalized β-lactams*
Willem Van Brabandt, Yves Dejaegher, and Norbert De Kimpe
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium
Abstract:
An easy synthesis of 4-(1- and 2-haloalkyl)azetidin-2-ones by a [2+2] cycloadditon protocol is described. Starting from these functionalized β-lactams, new pathways toward bicyclic β-lactams were developed via intramolecular nucleophilic substitutions and radical cyclizations. 4-(1- and 2-Haloalkyl)azetidin-2-ones also proved to be very useful starting products in the synthesis of various highly substituted aziridines, azetidines, and alkenoates.
Keywords: alkenoates; azetidines; azetines; aziridines; bicyclic β-lactams; β-lactams.
*Paper based on a presentation at the 7th IUPAC International Conference on Heteroatom Chemistry (ICHAC-7), Shanghai, China, 21-25 August 2004. Other presentations are published in this issue, pp. 1985-2132.