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Use of functionalized β-lactams as building blocks in heterocyclic chemistry

Matthias D'hooghe (UGent) , Stijn Dekeukeleire (UGent) , Erika Leemans (UGent) and Norbert De Kimpe (UGent)
(2010) PURE AND APPLIED CHEMISTRY. 82(9). p.1749-1759
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Abstract
beta-Lactams represent flexible building blocks suitable for the preparation of a large variety of nitrogen-containing target compounds. In the present study, the formerly neglected synthetic potential of 4-haloalkyl-beta-lactams has been elaborated in detail with a focus on the preparation of different mono- and bicyclic heterocycles. A first approach involved ring transformations of these halogenated building blocks toward stereodefined aziridines, azetidines, pyrrolidines, and piperidines via intermediate aziridinium or azetidinium ions. In a second part, novel and stereoselective entries into 1,4- and 3,4-fused bicyclic beta-lactams were developed through either a radical or an ionic cyclization protocol. Furthermore, the ring enlargement of halogenated beta-lactams into functionalized mono- and bicyclic pyrrolidin-2-ones was established as the aza-analog of the cyclobutylmethylcarbenium ion to cyclopentylcarbenium ion rearrangement. Finally, chiral versions toward azetidin-2-ones and ring transformation products were elaborated, involving the synthesis of 3(S)-alkoxy-4(S)-[1(S)-chloroethyl]azetidin-2-ones and the preparation of bicyclic beta-lactams annelated to piperazines, morpholines, and diazepanes.
Keywords
STEREOSELECTIVE-SYNTHESIS, IMINE CYCLOADDITION REACTION, ASYMMETRIC-SYNTHESIS, STAUDINGER REACTION, STEREOCONTROLLED SYNTHESIS, SYNTHON METHOD, GAMMA-LACTAMS, AMINO ACIDS, AZETIDINES, TRANSFORMATION, pyrrolidines, stereoselectivity, azetidines, aziridines, beta-lactams, gamma-lactams, piperidines

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Citation

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

MLA
D’hooghe, Matthias, Stijn Dekeukeleire, Erika Leemans, et al. “Use of Functionalized Β-lactams as Building Blocks in Heterocyclic Chemistry.” PURE AND APPLIED CHEMISTRY 82.9 (2010): 1749–1759. Print.
APA
D’hooghe, M., Dekeukeleire, S., Leemans, E., & De Kimpe, N. (2010). Use of functionalized β-lactams as building blocks in heterocyclic chemistry. PURE AND APPLIED CHEMISTRY, 82(9), 1749–1759.
Chicago author-date
D’hooghe, Matthias, Stijn Dekeukeleire, Erika Leemans, and Norbert De Kimpe. 2010. “Use of Functionalized Β-lactams as Building Blocks in Heterocyclic Chemistry.” Pure and Applied Chemistry 82 (9): 1749–1759.
Chicago author-date (all authors)
D’hooghe, Matthias, Stijn Dekeukeleire, Erika Leemans, and Norbert De Kimpe. 2010. “Use of Functionalized Β-lactams as Building Blocks in Heterocyclic Chemistry.” Pure and Applied Chemistry 82 (9): 1749–1759.
Vancouver
1.
D’hooghe M, Dekeukeleire S, Leemans E, De Kimpe N. Use of functionalized β-lactams as building blocks in heterocyclic chemistry. PURE AND APPLIED CHEMISTRY. 2010;82(9):1749–59.
IEEE
[1]
M. D’hooghe, S. Dekeukeleire, E. Leemans, and N. De Kimpe, “Use of functionalized β-lactams as building blocks in heterocyclic chemistry,” PURE AND APPLIED CHEMISTRY, vol. 82, no. 9, pp. 1749–1759, 2010.
@article{1091551,
  abstract     = {beta-Lactams represent flexible building blocks suitable for the preparation of a large variety of nitrogen-containing target compounds. In the present study, the formerly neglected synthetic potential of 4-haloalkyl-beta-lactams has been elaborated in detail with a focus on the preparation of different mono- and bicyclic heterocycles. A first approach involved ring transformations of these halogenated building blocks toward stereodefined aziridines, azetidines, pyrrolidines, and piperidines via intermediate aziridinium or azetidinium ions. In a second part, novel and stereoselective entries into 1,4- and 3,4-fused bicyclic beta-lactams were developed through either a radical or an ionic cyclization protocol. Furthermore, the ring enlargement of halogenated beta-lactams into functionalized mono- and bicyclic pyrrolidin-2-ones was established as the aza-analog of the cyclobutylmethylcarbenium ion to cyclopentylcarbenium ion rearrangement. Finally, chiral versions toward azetidin-2-ones and ring transformation products were elaborated, involving the synthesis of 3(S)-alkoxy-4(S)-[1(S)-chloroethyl]azetidin-2-ones and the preparation of bicyclic beta-lactams annelated to piperazines, morpholines, and diazepanes.},
  author       = {D'hooghe, Matthias and Dekeukeleire, Stijn and Leemans, Erika and De Kimpe, Norbert},
  issn         = {0033-4545},
  journal      = {PURE AND APPLIED CHEMISTRY},
  keywords     = {STEREOSELECTIVE-SYNTHESIS,IMINE CYCLOADDITION REACTION,ASYMMETRIC-SYNTHESIS,STAUDINGER REACTION,STEREOCONTROLLED SYNTHESIS,SYNTHON METHOD,GAMMA-LACTAMS,AMINO ACIDS,AZETIDINES,TRANSFORMATION,pyrrolidines,stereoselectivity,azetidines,aziridines,beta-lactams,gamma-lactams,piperidines},
  language     = {eng},
  number       = {9},
  pages        = {1749--1759},
  title        = {Use of functionalized β-lactams as building blocks in heterocyclic chemistry},
  url          = {http://dx.doi.org/10.1351/PAC-CON-09-09-39},
  volume       = {82},
  year         = {2010},
}

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