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Microwave-assisted regioselective ring opening of non-activated aziridines by lithium aluminium hydride

Sonja Stanković UGent, Matthias D'hooghe UGent and Norbert De Kimpe UGent (2010) ORGANIC & BIOMOLECULAR CHEMISTRY. 8(19). p.4266-4273
abstract
A new synthetic protocol for the LiAlH4-promoted reduction of non-activated aziridines under microwave conditions was developed. Thus, ring opening of 2-(acetoxymethyl)aziridines provided the corresponding beta-amino alcohols, which were then used as eligible substrates in the synthesis of 5-methylmorpholin-2-ones via condensation with glyoxal in THF. The same procedure was applied for the preparation of novel 5(R)- and 5(S)-methylmorpholin-2-ones starting from the corresponding enantiopure 2-(hydroxymethyl)aziridines. Additionally, 2-(methoxymethyl)- and 2-(phenoxymethyl)aziridines were treated with LiAlH4 under microwave irradiation, giving rise to either isopropylamines or 1-methoxypropan-2-amines depending on the reaction conditions.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
VICINAL AMINO-ALCOHOLS, HALOGENATED IMINO COMPOUNDS, ASYMMETRIC-SYNTHESIS, ENANTIOMERICALLY PURE, EFFICIENT SYNTHESIS, CHIRAL AZIRIDINES, FACILE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, STEREOSPECIFIC SYNTHESIS, PROTEASE INHIBITORS
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
8
issue
19
pages
4266 - 4273
Web of Science type
Article
Web of Science id
000282474300013
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.451 (2010)
JCR rank
12/56 (2010)
JCR quartile
1 (2010)
ISSN
1477-0520
DOI
10.1039/c004960c
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1091561
handle
http://hdl.handle.net/1854/LU-1091561
date created
2010-12-22 16:47:26
date last changed
2011-11-01 00:30:56
@article{1091561,
  abstract     = {A new synthetic protocol for the LiAlH4-promoted reduction of non-activated aziridines under microwave conditions was developed. Thus, ring opening of 2-(acetoxymethyl)aziridines provided the corresponding beta-amino alcohols, which were then used as eligible substrates in the synthesis of 5-methylmorpholin-2-ones via condensation with glyoxal in THF. The same procedure was applied for the preparation of novel 5(R)- and 5(S)-methylmorpholin-2-ones starting from the corresponding enantiopure 2-(hydroxymethyl)aziridines. Additionally, 2-(methoxymethyl)- and 2-(phenoxymethyl)aziridines were treated with LiAlH4 under microwave irradiation, giving rise to either isopropylamines or 1-methoxypropan-2-amines depending on the reaction conditions.},
  author       = {Stankovi\'{c}, Sonja and D'hooghe, Matthias and De Kimpe, Norbert},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  keyword      = {VICINAL AMINO-ALCOHOLS,HALOGENATED IMINO COMPOUNDS,ASYMMETRIC-SYNTHESIS,ENANTIOMERICALLY PURE,EFFICIENT SYNTHESIS,CHIRAL AZIRIDINES,FACILE SYNTHESIS,STEREOSELECTIVE-SYNTHESIS,STEREOSPECIFIC SYNTHESIS,PROTEASE INHIBITORS},
  language     = {eng},
  number       = {19},
  pages        = {4266--4273},
  title        = {Microwave-assisted regioselective ring opening of non-activated aziridines by lithium aluminium hydride},
  url          = {http://dx.doi.org/10.1039/c004960c},
  volume       = {8},
  year         = {2010},
}

Chicago
Stanković, Sonja, Matthias D’hooghe, and Norbert De Kimpe. 2010. “Microwave-assisted Regioselective Ring Opening of Non-activated Aziridines by Lithium Aluminium Hydride.” Organic & Biomolecular Chemistry 8 (19): 4266–4273.
APA
Stanković, Sonja, D’hooghe, M., & De Kimpe, N. (2010). Microwave-assisted regioselective ring opening of non-activated aziridines by lithium aluminium hydride. ORGANIC & BIOMOLECULAR CHEMISTRY, 8(19), 4266–4273.
Vancouver
1.
Stanković S, D’hooghe M, De Kimpe N. Microwave-assisted regioselective ring opening of non-activated aziridines by lithium aluminium hydride. ORGANIC & BIOMOLECULAR CHEMISTRY. 2010;8(19):4266–73.
MLA
Stanković, Sonja, Matthias D’hooghe, and Norbert De Kimpe. “Microwave-assisted Regioselective Ring Opening of Non-activated Aziridines by Lithium Aluminium Hydride.” ORGANIC & BIOMOLECULAR CHEMISTRY 8.19 (2010): 4266–4273. Print.