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Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks

(2017) ORGANIC & BIOMOLECULAR CHEMISTRY. 15(22). p.4816-4821
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Organization
Abstract
The Co-2(CO)(8)-catalyzed carbonylation of different classes of non-activated aziridines with diverse substitution patterns was investigated. Special attention was devoted to selectivity issues and reaction optimization. This study resulted in the regio-and stereospecific synthesis of 24 novel beta-lactam target structures in high yields on a multigram scale. The synthetic potential of the newly obtained azetidin-2-ones was illustrated via ring-expansion, ring-closure, and/or side chain-functionalization protocols to provide a straightforward entry to novel pyrrolidines, C-fused bi- and tricyclic beta-lactams and monocyclic carbapenem analogs.
Keywords
RING EXPANSION, DIASTEREOSELECTIVE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, ASYMMETRIC-SYNTHESIS, STAUDINGER REACTION, REACTION-MECHANISM, ALIPHATIC-AMINES, TRANSFORMATION, REARRANGEMENT, SUBSTITUTION

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MLA
Piens, Nicola et al. “Cobalt Carbonyl-catalyzed Carbonylation of Functionalized Aziridines to Versatile Β-lactam Building Blocks.” ORGANIC & BIOMOLECULAR CHEMISTRY 15.22 (2017): 4816–4821. Print.
APA
Piens, N., Van Hecke, K., Vogt, D., & D’hooghe, M. (2017). Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks. ORGANIC & BIOMOLECULAR CHEMISTRY, 15(22), 4816–4821.
Chicago author-date
Piens, Nicola, Kristof Van Hecke, Dieter Vogt, and Matthias D’hooghe. 2017. “Cobalt Carbonyl-catalyzed Carbonylation of Functionalized Aziridines to Versatile Β-lactam Building Blocks.” Organic & Biomolecular Chemistry 15 (22): 4816–4821.
Chicago author-date (all authors)
Piens, Nicola, Kristof Van Hecke, Dieter Vogt, and Matthias D’hooghe. 2017. “Cobalt Carbonyl-catalyzed Carbonylation of Functionalized Aziridines to Versatile Β-lactam Building Blocks.” Organic & Biomolecular Chemistry 15 (22): 4816–4821.
Vancouver
1.
Piens N, Van Hecke K, Vogt D, D’hooghe M. Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks. ORGANIC & BIOMOLECULAR CHEMISTRY. 2017;15(22):4816–21.
IEEE
[1]
N. Piens, K. Van Hecke, D. Vogt, and M. D’hooghe, “Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 15, no. 22, pp. 4816–4821, 2017.
@article{8522716,
  abstract     = {The Co-2(CO)(8)-catalyzed carbonylation of different classes of non-activated aziridines with diverse substitution patterns was investigated. Special attention was devoted to selectivity issues and reaction optimization. This study resulted in the regio-and stereospecific synthesis of 24 novel beta-lactam target structures in high yields on a multigram scale. The synthetic potential of the newly obtained azetidin-2-ones was illustrated via ring-expansion, ring-closure, and/or side chain-functionalization protocols to provide a straightforward entry to novel pyrrolidines, C-fused bi- and tricyclic beta-lactams and monocyclic carbapenem analogs.},
  author       = {Piens, Nicola and Van Hecke, Kristof and Vogt, Dieter and D'hooghe, Matthias},
  issn         = {1477-0520},
  journal      = {ORGANIC & BIOMOLECULAR CHEMISTRY},
  keywords     = {RING EXPANSION,DIASTEREOSELECTIVE SYNTHESIS,STEREOSELECTIVE-SYNTHESIS,ASYMMETRIC-SYNTHESIS,STAUDINGER REACTION,REACTION-MECHANISM,ALIPHATIC-AMINES,TRANSFORMATION,REARRANGEMENT,SUBSTITUTION},
  language     = {eng},
  number       = {22},
  pages        = {4816--4821},
  title        = {Cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to versatile β-lactam building blocks},
  url          = {http://dx.doi.org/10.1039/c7ob00832e},
  volume       = {15},
  year         = {2017},
}

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