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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
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.
Please use this url to cite or link to this publication:
author
organization
alternative title
Use of functionalized beta-lactams as building blocks in heterocyclic chemistry
year
type
journalArticle (original)
publication status
published
subject
keyword
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
journal title
PURE AND APPLIED CHEMISTRY
Pure Appl. Chem.
volume
82
issue
9
pages
1749 - 1759
Web of Science type
Article
Web of Science id
000281367700003
JCR category
CHEMISTRY, MULTIDISCIPLINARY
JCR impact factor
2.128 (2010)
JCR rank
42/142 (2010)
JCR quartile
2 (2010)
ISSN
0033-4545
DOI
10.1351/PAC-CON-09-09-39
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1091551
handle
http://hdl.handle.net/1854/LU-1091551
date created
2010-12-22 16:40:57
date last changed
2010-12-23 11:02:45
@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},
  keyword      = {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 \ensuremath{\beta}-lactams as building blocks in heterocyclic chemistry},
  url          = {http://dx.doi.org/10.1351/PAC-CON-09-09-39},
  volume       = {82},
  year         = {2010},
}

Chicago
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.
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.
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.
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.