Ghent University Academic Bibliography

Advanced

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

Nicola Piens, Hannelore Goossens, Dietmar Hertsen UGent, Sari Deketelaere UGent, Lieselotte Crul, Lotte Demeurisse, Jelle De Moor, Elias Van Den Broeck UGent, Karen Mollet, Kristof Van Hecke UGent, et al. (2017) CHEMISTRY-A EUROPEAN JOURNAL. 23(71). p.18002-18009
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.
Please use this url to cite or link to this publication:
author
organization
alternative title
Reactivity of 3-oxo-beta-lactams with respect to primary amines : an experimental and computational approach
year
type
journalArticle (original)
publication status
published
subject
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
journal title
CHEMISTRY-A EUROPEAN JOURNAL
Chem.-Eur. J.
volume
23
issue
71
pages
18002 - 18009
Web of Science type
Article
Web of Science id
000418356700023
ISSN
0947-6539
1521-3765
DOI
10.1002/chem.201703852
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
8534081
handle
http://hdl.handle.net/1854/LU-8534081
date created
2017-10-12 14:14:31
date last changed
2018-02-28 10:31:23
@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},
}

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.