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Synthesis of 3,4-fused bicyclic β-lactams and their transformation into methyl cis-3-aminotetrahydrofuran-2-carboxylates

Erika Leemans UGent, Matthias D'hooghe UGent, Yves Dejaegher, Karl Törnroos and Norbert De Kimpe UGent (2010) EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. p.352-358
abstract
cis-3-Benzyloxy-4-(2-bromo-1,1-dimethylethyl)azetidin-2-ones were transformed into the corresponding 3-hydroxy-beta-lactams through hydrogenolysis of the benzyl ether substituent, followed by formation of novel cis-2-oxa-6-azabicyclo[3.2.0] heptan-7-ones by intramolecular nucleophilic substitution utilizing triethylamine in benzene. The conversion of the latter cis-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones into cis-3-aminotetrahydrofuran-2-carboxylates was accomplished by means of acidic methanolysis. In this paper, the first straightforward transformation of cis-azetidin-2-ones into cis-3-aminotetrahydrofuran-2-carboxylates via bicychc beta-lactams is reported.
Please use this url to cite or link to this publication:
author
organization
alternative title
Synthesis of 3,4-fused bicyclic beta-lactams and their transformation into methyl cis-3-aminotetrahydrofuran-2-carboxylates
year
type
journalArticle (original)
publication status
published
subject
keyword
IMINE CYCLOADDITION REACTION, ASYMMETRIC-SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, BUILDING-BLOCKS, AMINO ACIDS, RADICAL CYCLIZATION, RING TRANSFORMATION, ENANTIOSELECTIVE SYNTHESIS, STAUDINGER REACTION, EFFICIENT SYNTHESIS, beta-Lactams, beta-Amino acids, Oxolanes, Cyclization, Stereoselectivity
journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Eur. J. Org. Chem.
issue
2
pages
352 - 358
Web of Science type
Article
Web of Science id
000274281000016
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.206 (2010)
JCR rank
13/56 (2010)
JCR quartile
1 (2010)
ISSN
1434-193X
DOI
10.1002/ejoc.200901110
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
852327
handle
http://hdl.handle.net/1854/LU-852327
date created
2010-02-05 08:45:11
date last changed
2011-07-12 13:50:42
@article{852327,
  abstract     = {cis-3-Benzyloxy-4-(2-bromo-1,1-dimethylethyl)azetidin-2-ones were transformed into the corresponding 3-hydroxy-beta-lactams through hydrogenolysis of the benzyl ether substituent, followed by formation of novel cis-2-oxa-6-azabicyclo[3.2.0] heptan-7-ones by intramolecular nucleophilic substitution utilizing triethylamine in benzene. The conversion of the latter cis-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones into cis-3-aminotetrahydrofuran-2-carboxylates was accomplished by means of acidic methanolysis. In this paper, the first straightforward transformation of cis-azetidin-2-ones into cis-3-aminotetrahydrofuran-2-carboxylates via bicychc beta-lactams is reported.},
  author       = {Leemans, Erika and D'hooghe, Matthias and Dejaegher, Yves and T{\"o}rnroos, Karl and De Kimpe, Norbert},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {IMINE CYCLOADDITION REACTION,ASYMMETRIC-SYNTHESIS,STEREOSELECTIVE-SYNTHESIS,BUILDING-BLOCKS,AMINO ACIDS,RADICAL CYCLIZATION,RING TRANSFORMATION,ENANTIOSELECTIVE SYNTHESIS,STAUDINGER REACTION,EFFICIENT SYNTHESIS,beta-Lactams,beta-Amino acids,Oxolanes,Cyclization,Stereoselectivity},
  language     = {eng},
  number       = {2},
  pages        = {352--358},
  title        = {Synthesis of 3,4-fused bicyclic \ensuremath{\beta}-lactams and their transformation into methyl cis-3-aminotetrahydrofuran-2-carboxylates},
  url          = {http://dx.doi.org/10.1002/ejoc.200901110},
  year         = {2010},
}

Chicago
Leemans, Erika, Matthias D’hooghe, Yves Dejaegher, Karl Törnroos, and Norbert De Kimpe. 2010. “Synthesis of 3,4-fused Bicyclic Β-lactams and Their Transformation into Methyl Cis-3-aminotetrahydrofuran-2-carboxylates.” European Journal of Organic Chemistry (2): 352–358.
APA
Leemans, E., D’hooghe, M., Dejaegher, Y., Törnroos, K., & De Kimpe, N. (2010). Synthesis of 3,4-fused bicyclic β-lactams and their transformation into methyl cis-3-aminotetrahydrofuran-2-carboxylates. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (2), 352–358.
Vancouver
1.
Leemans E, D’hooghe M, Dejaegher Y, Törnroos K, De Kimpe N. Synthesis of 3,4-fused bicyclic β-lactams and their transformation into methyl cis-3-aminotetrahydrofuran-2-carboxylates. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2010;(2):352–8.
MLA
Leemans, Erika, Matthias D’hooghe, Yves Dejaegher, et al. “Synthesis of 3,4-fused Bicyclic Β-lactams and Their Transformation into Methyl Cis-3-aminotetrahydrofuran-2-carboxylates.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2 (2010): 352–358. Print.