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Piens N, Goossens H, Hertsen D, et al. Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines-An Experimental and Computational Approach. Chemistry. 2017;23(71):18002-18009doi: 10.1002/chem.201703852.
Piens, N., Goossens, H., Hertsen, D., Deketelaere, S., Crul, L., Demeurisse, L., De Moor, J., Van den Broeck, E., Mollet, K., Van Hecke, K., Van Speybroeck, V., & D'hooghe, M. (2017). Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines-An Experimental and Computational Approach. Chemistry (Weinheim an der Bergstrasse, Germany), 23(71), 18002-18009. https://doi.org/10.1002/chem.201703852
Piens, Nicola, et al. "Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines-An Experimental and Computational Approach." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,71 (2017): 18002-18009. doi: https://doi.org/10.1002/chem.201703852
Piens N, Goossens H, Hertsen D, Deketelaere S, Crul L, Demeurisse L, De Moor J, Van den Broeck E, Mollet K, Van Hecke K, Van Speybroeck V, D'hooghe M. Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines-An Experimental and Computational Approach. Chemistry. 2017 Dec 19;23(71):18002-18009. doi: 10.1002/chem.201703852. Epub 2017 Dec 04. PMID: 29024090.
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Chemistry. 2017 Dec 19;23(71):18002-18009. doi: 10.1002/chem.201703852. Epub 2017 Dec 04.

Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines-An Experimental and Computational Approach.

Chemistry (Weinheim an der Bergstrasse, Germany)

Nicola Piens, Hannelore Goossens, Dietmar Hertsen, Sari Deketelaere, Lieselotte Crul, Lotte Demeurisse, Jelle De Moor, Elias Van den Broeck, Karen Mollet, Kristof Van Hecke, Veronique Van Speybroeck, Matthias D'hooghe

Affiliations

  1. SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium.
  2. Center for Molecular Modeling, Ghent University, Technologiepark 903, 9052, Zwijnaarde, Belgium.
  3. XStruct, Department of Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281-S3, 9000, Ghent, Belgium.

PMID: 29024090 DOI: 10.1002/chem.201703852

Abstract

The reactivity of 3-oxo-β-lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino-β-lactams (through dehydration), α-aminoamides (through CO elimination), or ethanediamides (through an unprecedented C3-C4 ring opening). In addition to the experimental results, the mechanisms and factors governing these peculiar transformations were also examined and elucidated by means of DFT calculations.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: density functional calculations; lactams; natural products; reaction mechanisms; structure elucidation

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