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Transformation of trans-4-aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-aryl-2-(ethylamino)propan-1-ols via intermediate 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines and trans-2-aryl-3-(hydroxymethyl)aziridines

Karen Mollet UGent, Matthias D'hooghe UGent and Norbert De Kimpe UGent (2011) JOURNAL OF ORGANIC CHEMISTRY. 76(1). p.264-269
abstract
trans-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were unexpectedly transformed into 3-aryl-2-(ethylamino)propan-1-ols using LiAlH4 in THF under reflux. A stepwise analysis showed that the initially formed 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines were converted into trans-2-aryl-3-(hydroxymethyl)aziridines, most probably via N-spiro bis-aziridinium intermediates, which were subsequently prone to undergo ring opening by LiAlH4 to afford 3-aryl-2-(ethylamino)propan-1-ols.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
STEREOSELECTIVE-SYNTHESIS, STAUDINGER REACTION, BUILDING-BLOCKS, ASYMMETRIC-SYNTHESIS, LACTAM SYNTHON METHOD, BETA-LACTAMS, RING EXPANSION, CONTAINING LIGANDS, AMINO-ACIDS, AZETIDINES
journal title
JOURNAL OF ORGANIC CHEMISTRY
J. Org. Chem.
volume
76
issue
1
pages
264 - 269
Web of Science type
Article
Web of Science id
000285704000029
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
4.45 (2011)
JCR rank
9/56 (2011)
JCR quartile
1 (2011)
ISSN
0022-3263
DOI
10.1021/jo1020932
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1234388
handle
http://hdl.handle.net/1854/LU-1234388
date created
2011-05-24 15:58:11
date last changed
2011-05-25 10:21:13
@article{1234388,
  abstract     = {trans-4-Aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were unexpectedly transformed into 3-aryl-2-(ethylamino)propan-1-ols using LiAlH4 in THF under reflux. A stepwise analysis showed that the initially formed 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines were converted into trans-2-aryl-3-(hydroxymethyl)aziridines, most probably via N-spiro bis-aziridinium intermediates, which were subsequently prone to undergo ring opening by LiAlH4 to afford 3-aryl-2-(ethylamino)propan-1-ols.},
  author       = {Mollet, Karen and D'hooghe, Matthias and De Kimpe, Norbert},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keyword      = {STEREOSELECTIVE-SYNTHESIS,STAUDINGER REACTION,BUILDING-BLOCKS,ASYMMETRIC-SYNTHESIS,LACTAM SYNTHON METHOD,BETA-LACTAMS,RING EXPANSION,CONTAINING LIGANDS,AMINO-ACIDS,AZETIDINES},
  language     = {eng},
  number       = {1},
  pages        = {264--269},
  title        = {Transformation of trans-4-aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-aryl-2-(ethylamino)propan-1-ols via intermediate 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines and trans-2-aryl-3-(hydroxymethyl)aziridines},
  url          = {http://dx.doi.org/10.1021/jo1020932},
  volume       = {76},
  year         = {2011},
}

Chicago
Mollet, Karen, Matthias D’hooghe, and Norbert De Kimpe. 2011. “Transformation of Trans-4-aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-aryl-2-(ethylamino)propan-1-ols via Intermediate 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines and Trans-2-aryl-3-(hydroxymethyl)aziridines.” Journal of Organic Chemistry 76 (1): 264–269.
APA
Mollet, K., D’hooghe, M., & De Kimpe, N. (2011). Transformation of trans-4-aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-aryl-2-(ethylamino)propan-1-ols via intermediate 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines and trans-2-aryl-3-(hydroxymethyl)aziridines. JOURNAL OF ORGANIC CHEMISTRY, 76(1), 264–269.
Vancouver
1.
Mollet K, D’hooghe M, De Kimpe N. Transformation of trans-4-aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-aryl-2-(ethylamino)propan-1-ols via intermediate 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines and trans-2-aryl-3-(hydroxymethyl)aziridines. JOURNAL OF ORGANIC CHEMISTRY. 2011;76(1):264–9.
MLA
Mollet, Karen, Matthias D’hooghe, and Norbert De Kimpe. “Transformation of Trans-4-aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-aryl-2-(ethylamino)propan-1-ols via Intermediate 1-(1-aryl-2-chloro-3-hydroxypropyl)aziridines and Trans-2-aryl-3-(hydroxymethyl)aziridines.” JOURNAL OF ORGANIC CHEMISTRY 76.1 (2011): 264–269. Print.