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Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone

Sara Kenis UGent, Matthias D'hooghe UGent, Guido Verniest UGent, Vinh Duc Nguyen, Anh Dang Thi Tuyet, Tuyen Van Nguyen and Norbert De Kimpe UGent (2011) ORGANIC & BIOMOLECULAR CHEMISTRY. 9(20). p.7217-7223
abstract
An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone via imination, alpha-chlorination, hydride reduction and ring closure was developed. In addition, novel primary beta-iodo amines were obtained by regioselective ring opening of these 2-(trifluoromethyl)aziridines using alkyl iodides, and their synthetic potential was demonstrated by converting them into novel alpha-CF(3)-beta-phenylethylamines upon treatment with lithium diphenylcuprate.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
RING-OPENING REACTIONS, HALOGENATED IMINO COMPOUNDS, MEDICINAL CHEMISTRY, ASYMMETRIC-SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, ORGANOFLUORINE CHEMISTRY, ORGANOMETALLIC REAGENTS, FLUORINE CHEMISTRY, CHIRAL AZIRIDINES, AMINO-ACIDS
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
9
issue
20
pages
7217 - 7223
Web of Science type
Article
Web of Science id
000295889900050
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.696 (2011)
JCR rank
11/56 (2011)
JCR quartile
1 (2011)
ISSN
1477-0520
DOI
10.1039/C1OB05813D
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1988642
handle
http://hdl.handle.net/1854/LU-1988642
date created
2012-01-17 09:27:31
date last changed
2012-06-18 00:30:44
@article{1988642,
  abstract     = {An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone via imination, alpha-chlorination, hydride reduction and ring closure was developed. In addition, novel primary beta-iodo amines were obtained by regioselective ring opening of these 2-(trifluoromethyl)aziridines using alkyl iodides, and their synthetic potential was demonstrated by converting them into novel alpha-CF(3)-beta-phenylethylamines upon treatment with lithium diphenylcuprate.},
  author       = {Kenis, Sara and D'hooghe, Matthias and Verniest, Guido and Nguyen, Vinh Duc and Tuyet, Anh Dang Thi and Nguyen, Tuyen Van and De Kimpe, Norbert},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  keyword      = {RING-OPENING REACTIONS,HALOGENATED IMINO COMPOUNDS,MEDICINAL CHEMISTRY,ASYMMETRIC-SYNTHESIS,STEREOSELECTIVE-SYNTHESIS,ORGANOFLUORINE CHEMISTRY,ORGANOMETALLIC REAGENTS,FLUORINE CHEMISTRY,CHIRAL AZIRIDINES,AMINO-ACIDS},
  language     = {eng},
  number       = {20},
  pages        = {7217--7223},
  title        = {Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone},
  url          = {http://dx.doi.org/10.1039/C1OB05813D},
  volume       = {9},
  year         = {2011},
}

Chicago
Kenis, Sara, Matthias D’hooghe, Guido Verniest, Vinh Duc Nguyen, Anh Dang Thi Tuyet, Tuyen Van Nguyen, and Norbert De Kimpe. 2011. “Straightforward Synthesis of 1-alkyl-2-(trifluoromethyl)aziridines Starting from 1,1,1-trifluoroacetone.” Organic & Biomolecular Chemistry 9 (20): 7217–7223.
APA
Kenis, S., D’hooghe, M., Verniest, G., Nguyen, V. D., Tuyet, A. D. T., Nguyen, T. V., & De Kimpe, N. (2011). Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone. ORGANIC & BIOMOLECULAR CHEMISTRY, 9(20), 7217–7223.
Vancouver
1.
Kenis S, D’hooghe M, Verniest G, Nguyen VD, Tuyet ADT, Nguyen TV, et al. Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone. ORGANIC & BIOMOLECULAR CHEMISTRY. 2011;9(20):7217–23.
MLA
Kenis, Sara, Matthias D’hooghe, Guido Verniest, et al. “Straightforward Synthesis of 1-alkyl-2-(trifluoromethyl)aziridines Starting from 1,1,1-trifluoroacetone.” ORGANIC & BIOMOLECULAR CHEMISTRY 9.20 (2011): 7217–7223. Print.