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Stereoselective synthesis of cis- and trans-4-acyl-β-lactams from vicinal diketones and ketoaldehydes

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Abstract

4-Acyl-β-lactams are important synthetic intermediates in both pharmaceutical and organic chemistry. Cis- and trans-4-acyl-β-lactams were synthesized stereoselectively from vicinal diketones via the formation of bulky and less bulky diimines as key intermediates, respectively. The diimines reacted with acyl chloride in the presence of triethylamine to give rise to the corresponding 4-imino-β-lactams, which were further hydrolyzed to afford 4-acyl-β-lactams. The cis- and trans selectivity is depended on the steric hindrance of the imine N-substituents. A series of cis-4-acyl-β-lactams were synthesized from vicinal ketoaldehydes via the formation of their monoimines and diimines as intermediates. Pyruvic aldehyde produced cis-4-acetyl-β-lactams and cis-4-formyl-β-lactams, respectively, through the reactions of its monoimine and diimine with acyl chlorides. Phenylglyoxal generated cis-4-benzoyl-β-lactams via its monoaldimine.

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  1. State Key Laboratory of Chemical Resource Engineering; Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing, 100029, China

    ZhiXin Wang & JiaXi Xu

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Wang, Z., Xu, J. Stereoselective synthesis of cis- and trans-4-acyl-β-lactams from vicinal diketones and ketoaldehydes. Sci. China Chem. 54, 1711–1717 (2011). https://doi.org/10.1007/s11426-011-4372-1

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