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Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates: application towards the synthesis of 2-(methoxycarbonyl)indolizidine

Matthias D'hooghe UGent, Kourosch Abbaspour Tehrani, Christophe Buyck and Norbert De Kimpe UGent (2010) ARKIVOC. p.93-101
abstract
Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine hydrobromide to methyl and ethyl acrylate in the presence of triethylamine afforded the corresponding 3-[2-(bromomethyl)piperidin-1-yl]propanoates and 3-[2-(2-bromoethyl)piperidin-1-yl]propanoates for the first time. Furthermore, methyl 3-[2-(bromomethyl)piperidin-1-yl]propanoate was converted into the novel 2-(methoxycarbonyl)indolizidine upon treatment with lithium diisopropylamide in THF. The latter ester was easily reduced by means of lithium aluminium hydride in diethyl ether, affording 2-(hydroxymethyl)indolizidine in high yield.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
ALPHA, ENANTIOSELECTIVE SYNTHESIS, BETA-ETHYLENIC COMPOUNDS, ELECTRON-DEFICIENT ALKENES, SOLVENT-FREE CONDITIONS, BETA-AMINO ACIDS, HETEROALICYCLIC AMINOALKANOL, AZA-MICHAEL ADDITION, indolizidines, piperidines, beta-amino esters, aza-Michael reaction, ASYMMETRIC-SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, CONVENIENT SYNTHESIS
journal title
ARKIVOC
Arkivoc
issue
3
issue title
Commemorative Issue in Honor of Prof. Benito Alcaide on the occasion of his 60th anniversary
pages
93 - 101
Web of Science type
Article
Web of Science id
000273559700009
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
1.096 (2010)
JCR rank
34/56 (2010)
JCR quartile
3 (2010)
ISSN
1551-7004
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
849673
handle
http://hdl.handle.net/1854/LU-849673
alternative location
http://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/2010/3/
date created
2010-02-02 15:35:35
date last changed
2010-02-10 10:28:05
@article{849673,
  abstract     = {Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine hydrobromide to methyl and ethyl acrylate in the presence of triethylamine afforded the corresponding 3-[2-(bromomethyl)piperidin-1-yl]propanoates and 3-[2-(2-bromoethyl)piperidin-1-yl]propanoates for the first time. Furthermore, methyl 3-[2-(bromomethyl)piperidin-1-yl]propanoate was converted into the novel 2-(methoxycarbonyl)indolizidine upon treatment with lithium diisopropylamide in THF. The latter ester was easily reduced by means of lithium aluminium hydride in diethyl ether, affording 2-(hydroxymethyl)indolizidine in high yield.},
  author       = {D'hooghe, Matthias and Abbaspour Tehrani, Kourosch and Buyck, Christophe and De Kimpe, Norbert},
  issn         = {1551-7004},
  journal      = {ARKIVOC},
  keyword      = {ALPHA,ENANTIOSELECTIVE SYNTHESIS,BETA-ETHYLENIC COMPOUNDS,ELECTRON-DEFICIENT ALKENES,SOLVENT-FREE CONDITIONS,BETA-AMINO ACIDS,HETEROALICYCLIC AMINOALKANOL,AZA-MICHAEL ADDITION,indolizidines,piperidines,beta-amino esters,aza-Michael reaction,ASYMMETRIC-SYNTHESIS,STEREOSELECTIVE-SYNTHESIS,CONVENIENT SYNTHESIS},
  language     = {eng},
  number       = {3},
  pages        = {93--101},
  title        = {Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates: application towards the synthesis of 2-(methoxycarbonyl)indolizidine},
  url          = {http://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/2010/3/},
  year         = {2010},
}

Chicago
D’hooghe, Matthias, Kourosch Abbaspour Tehrani, Christophe Buyck, and Norbert De Kimpe. 2010. “Conjugate Addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to Alkyl Acrylates: Application Towards the Synthesis of 2-(methoxycarbonyl)indolizidine.” Arkivoc (3): 93–101.
APA
D’hooghe, M., Abbaspour Tehrani, K., Buyck, C., & De Kimpe, N. (2010). Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates: application towards the synthesis of 2-(methoxycarbonyl)indolizidine. ARKIVOC, (3), 93–101.
Vancouver
1.
D’hooghe M, Abbaspour Tehrani K, Buyck C, De Kimpe N. Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to alkyl acrylates: application towards the synthesis of 2-(methoxycarbonyl)indolizidine. ARKIVOC. 2010;(3):93–101.
MLA
D’hooghe, Matthias, Kourosch Abbaspour Tehrani, Christophe Buyck, et al. “Conjugate Addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine to Alkyl Acrylates: Application Towards the Synthesis of 2-(methoxycarbonyl)indolizidine.” ARKIVOC 3 (2010): 93–101. Print.