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Chemical and enzymatic synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and their conversion into δ-lactams and γ-lactones

Karel Vervisch UGent, Matthias D'hooghe UGent, Floris PJT Rutjes and Norbert De Kimpe UGent (2012) ORGANIC LETTERS. 14(1). p.106-109
abstract
Treatment of 1-arylmethyl-2-(2-cyanoethyl)aziridines with a nitrile hydratase afforded the corresponding 2-(2-carbamoylethyl)aziridines, which underwent rearrangement into 5-hydroxypiperidin-2-ones upon heating under microwave irradiation. In addition, treatment of 2-(2-cyanoethyl)aziridines with a nitrilase selectively afforded 5-hydroxypiperidin-2-ones in good yields. On the other hand, chemical hydrolysis of 2-(2-cyanoethyl)aziridines using KOH In EtOH/H2O furnished the corresponding potassium 3-(aziridin-2-yl)propanoates, which, upon acidification with acetic acid, smoothly rearranged into 4-(aminomethyl)butyrolactones.
Please use this url to cite or link to this publication:
author
organization
alternative title
Chemical and enzymatic synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and their conversion into delta-lactams and gamma-lactones
year
type
journalArticle (original)
publication status
published
subject
keyword
BETA-AMINO ACIDS, RING-OPENING REACTIONS, STEREOSELECTIVE-SYNTHESIS, ORGANIC-SYNTHESIS, NITRILE, TRANSFORMATION, DERIVATIVES, ENANTIOPURE, ENZYMES, BIOTRANSFORMATIONS
journal title
ORGANIC LETTERS
Org. Lett.
volume
14
issue
1
pages
106 - 109
Web of Science type
Article
Web of Science id
000298828500028
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
6.142 (2012)
JCR rank
5/55 (2012)
JCR quartile
1 (2012)
ISSN
1523-7060
DOI
10.1021/ol202888j
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1991755
handle
http://hdl.handle.net/1854/LU-1991755
date created
2012-01-17 16:55:54
date last changed
2012-09-28 13:53:24
@article{1991755,
  abstract     = {Treatment of 1-arylmethyl-2-(2-cyanoethyl)aziridines with a nitrile hydratase afforded the corresponding 2-(2-carbamoylethyl)aziridines, which underwent rearrangement into 5-hydroxypiperidin-2-ones upon heating under microwave irradiation. In addition, treatment of 2-(2-cyanoethyl)aziridines with a nitrilase selectively afforded 5-hydroxypiperidin-2-ones in good yields. On the other hand, chemical hydrolysis of 2-(2-cyanoethyl)aziridines using KOH In EtOH/H2O furnished the corresponding potassium 3-(aziridin-2-yl)propanoates, which, upon acidification with acetic acid, smoothly rearranged into 4-(aminomethyl)butyrolactones.},
  author       = {Vervisch, Karel and D'hooghe, Matthias and Rutjes, Floris PJT and De Kimpe, Norbert},
  issn         = {1523-7060},
  journal      = {ORGANIC LETTERS},
  keyword      = {BETA-AMINO ACIDS,RING-OPENING REACTIONS,STEREOSELECTIVE-SYNTHESIS,ORGANIC-SYNTHESIS,NITRILE,TRANSFORMATION,DERIVATIVES,ENANTIOPURE,ENZYMES,BIOTRANSFORMATIONS},
  language     = {eng},
  number       = {1},
  pages        = {106--109},
  title        = {Chemical and enzymatic synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and their conversion into \ensuremath{\delta}-lactams and \ensuremath{\gamma}-lactones},
  url          = {http://dx.doi.org/10.1021/ol202888j},
  volume       = {14},
  year         = {2012},
}

Chicago
Vervisch, Karel, Matthias D’hooghe, Floris PJT Rutjes, and Norbert De Kimpe. 2012. “Chemical and Enzymatic Synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and Their Conversion into Δ-lactams and Γ-lactones.” Organic Letters 14 (1): 106–109.
APA
Vervisch, K., D’hooghe, M., Rutjes, F. P., & De Kimpe, N. (2012). Chemical and enzymatic synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and their conversion into δ-lactams and γ-lactones. ORGANIC LETTERS, 14(1), 106–109.
Vancouver
1.
Vervisch K, D’hooghe M, Rutjes FP, De Kimpe N. Chemical and enzymatic synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and their conversion into δ-lactams and γ-lactones. ORGANIC LETTERS. 2012;14(1):106–9.
MLA
Vervisch, Karel, Matthias D’hooghe, Floris PJT Rutjes, et al. “Chemical and Enzymatic Synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and Their Conversion into Δ-lactams and Γ-lactones.” ORGANIC LETTERS 14.1 (2012): 106–109. Print.