Advanced search
1 file | 11.70 MB

Carbonylation of aziridines as a powerful tool for the synthesis of functionalized β-lactams

Nicola Piens (UGent) and Matthias D'hooghe (UGent)
Author
Organization
Abstract
Within heterocyclic chemistry, beta-lactams comprise an extraordinary class of strained compounds, recognized for their biological importance as potent antibiotics and their chemical value as flexible building blocks for the construction of diverse nitrogen-containing structures. Among the synthetic routes available to access this interesting scaffold, the carbonylation of aziridines, in which carbon monoxide is inserted into one of the ring carbon-nitrogen bonds, is praised for its efficiency and remarkable regio- and stereoselectivity. This review provides a comprehensive overview of aziridine-to-azetidin-2-one carbonylation studies. The protocols are categorized according to the different transition metals (i.e. rhodium, palladium, nickel, iron, and cobalt) that have been employed (in a catalytic or stoichiometric amount) to effect this transformation.
Keywords
beta-Lactams, Aziridines, Carbonylation, Homogeneous catalysis, Ring expansion, ENOLATE IMINE CONDENSATION, CATALYZED RING EXPANSION, BUILDING-BLOCKS, ASYMMETRIC-SYNTHESIS, KINUGASA REACTION, DIASTEREOSELECTIVE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, THERMODYNAMIC PREFERENCE, STAUDINGER REACTION, KINETIC RESOLUTION

Downloads

  • Aziridine-to-β-lactam carbonylation (revised).doc
    • full text
    • |
    • open access
    • |
    • application/msword
    • |
    • 11.70 MB

Citation

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

Chicago
Piens, Nicola, and Matthias D’hooghe. 2017. “Carbonylation of Aziridines as a Powerful Tool for the Synthesis of Functionalized Β-lactams.” European Journal of Organic Chemistry 40: 5943–5960.
APA
Piens, N., & D’hooghe, M. (2017). Carbonylation of aziridines as a powerful tool for the synthesis of functionalized β-lactams. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 40, 5943–5960.
Vancouver
1.
Piens N, D’hooghe M. Carbonylation of aziridines as a powerful tool for the synthesis of functionalized β-lactams. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2017;40:5943–60.
MLA
Piens, Nicola, and Matthias D’hooghe. “Carbonylation of Aziridines as a Powerful Tool for the Synthesis of Functionalized Β-lactams.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 40 (2017): 5943–5960. Print.
@article{8528783,
  abstract     = {Within heterocyclic chemistry, beta-lactams comprise an extraordinary class of strained compounds, recognized for their biological importance as potent antibiotics and their chemical value as flexible building blocks for the construction of diverse nitrogen-containing structures. Among the synthetic routes available to access this interesting scaffold, the carbonylation of aziridines, in which carbon monoxide is inserted into one of the ring carbon-nitrogen bonds, is praised for its efficiency and remarkable regio- and stereoselectivity. This review provides a comprehensive overview of aziridine-to-azetidin-2-one carbonylation studies. The protocols are categorized according to the different transition metals (i.e. rhodium, palladium, nickel, iron, and cobalt) that have been employed (in a catalytic or stoichiometric amount) to effect this transformation.},
  author       = {Piens, Nicola and D'hooghe, Matthias},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {beta-Lactams,Aziridines,Carbonylation,Homogeneous catalysis,Ring expansion,ENOLATE IMINE CONDENSATION,CATALYZED RING EXPANSION,BUILDING-BLOCKS,ASYMMETRIC-SYNTHESIS,KINUGASA REACTION,DIASTEREOSELECTIVE SYNTHESIS,STEREOSELECTIVE-SYNTHESIS,THERMODYNAMIC PREFERENCE,STAUDINGER REACTION,KINETIC RESOLUTION},
  language     = {eng},
  pages        = {5943--5960},
  title        = {Carbonylation of aziridines as a powerful tool for the synthesis of functionalized β-lactams},
  url          = {http://dx.doi.org/10.1002/ejoc.201700698},
  volume       = {40},
  year         = {2017},
}

Altmetric
View in Altmetric
Web of Science
Times cited: