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Reactivity of 3-oxo-β-lactams with respect to primary amines : an experimental and computational approach

(2017) CHEMISTRY-A EUROPEAN JOURNAL. 23(71). p.18002-18009
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Abstract
The reactivity of 3-oxo--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--lactams (through dehydration), -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.
Keywords
density functional calculations, lactams, natural products, reaction mechanisms, structure elucidation, DENSITY-FUNCTIONAL THEORY, TRICYCLIC-BETA-LACTAMS, BUILDING-BLOCKS, STEREOCONTROLLED SYNTHESIS, ASYMMETRIC-SYNTHESIS, BENZYL 6-OXOPENICILLANATE, STEREOSELECTIVE-SYNTHESIS, NONCOVALENT INTERACTIONS, THERMOCHEMICAL KINETICS, HETEROCYCLIC CHEMISTRY

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Citation

Please use this url to cite or link to this publication:

Chicago
Piens, Nicola, Hannelore Goossens, Dietmar Hertsen, Sari Deketelaere, Lieselotte Crul, Lotte Demeurisse, Jelle De Moor, et al. 2017. “Reactivity of 3-oxo-β-lactams with Respect to Primary Amines : an Experimental and Computational Approach.” Chemistry-a European Journal 23 (71): 18002–18009.
APA
Piens, N., Goossens, H., Hertsen, D., Deketelaere, S., Crul, L., Demeurisse, L., De Moor, J., et al. (2017). Reactivity of 3-oxo-β-lactams with respect to primary amines : an experimental and computational approach. CHEMISTRY-A EUROPEAN JOURNAL, 23(71), 18002–18009.
Vancouver
1.
Piens N, Goossens H, Hertsen D, Deketelaere S, Crul L, Demeurisse L, et al. Reactivity of 3-oxo-β-lactams with respect to primary amines : an experimental and computational approach. CHEMISTRY-A EUROPEAN JOURNAL. 2017;23(71):18002–9.
MLA
Piens, Nicola, Hannelore Goossens, Dietmar Hertsen, et al. “Reactivity of 3-oxo-β-lactams with Respect to Primary Amines : an Experimental and Computational Approach.” CHEMISTRY-A EUROPEAN JOURNAL 23.71 (2017): 18002–18009. Print.
@article{8534081,
  abstract     = {The reactivity of 3-oxo--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--lactams (through dehydration), -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.},
  author       = {Piens, Nicola and Goossens, Hannelore and Hertsen, Dietmar and Deketelaere, Sari and Crul, Lieselotte and Demeurisse, Lotte and De Moor, Jelle and Van Den Broeck, Elias and Mollet, Karen and Van Hecke, Kristof and Van Speybroeck, Veronique and D'hooghe, Matthias},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keyword      = {density functional calculations,lactams,natural products,reaction mechanisms,structure elucidation,DENSITY-FUNCTIONAL THEORY,TRICYCLIC-BETA-LACTAMS,BUILDING-BLOCKS,STEREOCONTROLLED SYNTHESIS,ASYMMETRIC-SYNTHESIS,BENZYL 6-OXOPENICILLANATE,STEREOSELECTIVE-SYNTHESIS,NONCOVALENT INTERACTIONS,THERMOCHEMICAL KINETICS,HETEROCYCLIC CHEMISTRY},
  language     = {eng},
  number       = {71},
  pages        = {18002--18009},
  title        = {Reactivity of 3-oxo-\ensuremath{\beta}-lactams with respect to primary amines : an experimental and computational approach},
  url          = {http://dx.doi.org/10.1002/chem.201703852},
  volume       = {23},
  year         = {2017},
}

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