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3-Imidoallenylphophonates: in situ formation and β-alkoxylation

Jan Berton UGent, Thomas Heugebaert UGent, Wouter Debrouwer and Christian Stevens UGent (2016) ORGANIC LETTERS. 18(2). p.208-2011
abstract
3-Imidoallenylphosphonates, allenes bearing both an electron-withdrawing and -donating group, were isolated for the first time. An alkoxy substituent was introduced into these unprecedented intermediates in a one-pot approach, yielding beta-functionalized aminophosphonates in excellent yields and short reaction times. The mechanistic insights gained are important additions to the domain of allene chemistry. Addition of biologically important molecules, including monoglycerides, amino acids, and nucleosides, proves the general applicability of the developed method.
Please use this url to cite or link to this publication:
author
organization
alternative title
3-Imidoallenylphophonates : in situ formation and beta-alkoxylation
year
type
journalArticle (original)
publication status
published
subject
keyword
PHOSPHITES, AMINO ALLENEPHOSPHONATES, ALCOHOLS, ALKYNES, (DIMETHYLAMINO)ALLENE, HYDROAMINATION, REARRANGEMENT, NUCLEOPHILES, ALLENAMIDES, CYCLIZATION
journal title
ORGANIC LETTERS
Org. Lett.
volume
18
issue
2
pages
208 - 2011
Web of Science type
Article
Web of Science id
000368563200016
ISSN
1523-7060
DOI
10.1021/acs.orglett.5b03314
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
7220759
handle
http://hdl.handle.net/1854/LU-7220759
date created
2016-05-18 21:54:11
date last changed
2016-12-19 15:42:10
@article{7220759,
  abstract     = {3-Imidoallenylphosphonates, allenes bearing both an electron-withdrawing and -donating group, were isolated for the first time. An alkoxy substituent was introduced into these unprecedented intermediates in a one-pot approach, yielding beta-functionalized aminophosphonates in excellent yields and short reaction times. The mechanistic insights gained are important additions to the domain of allene chemistry. Addition of biologically important molecules, including monoglycerides, amino acids, and nucleosides, proves the general applicability of the developed method.},
  author       = {Berton, Jan and Heugebaert, Thomas and Debrouwer, Wouter and Stevens, Christian},
  issn         = {1523-7060},
  journal      = {ORGANIC LETTERS},
  keyword      = {PHOSPHITES,AMINO ALLENEPHOSPHONATES,ALCOHOLS,ALKYNES,(DIMETHYLAMINO)ALLENE,HYDROAMINATION,REARRANGEMENT,NUCLEOPHILES,ALLENAMIDES,CYCLIZATION},
  language     = {eng},
  number       = {2},
  pages        = {208--2011},
  title        = {3-Imidoallenylphophonates: in situ formation and \ensuremath{\beta}-alkoxylation},
  url          = {http://dx.doi.org/10.1021/acs.orglett.5b03314},
  volume       = {18},
  year         = {2016},
}

Chicago
Berton, Jan, Thomas Heugebaert, Wouter Debrouwer, and Christian Stevens. 2016. “3-Imidoallenylphophonates: In Situ Formation and Β-alkoxylation.” Organic Letters 18 (2): 208–2011.
APA
Berton, J., Heugebaert, T., Debrouwer, W., & Stevens, C. (2016). 3-Imidoallenylphophonates: in situ formation and β-alkoxylation. ORGANIC LETTERS, 18(2), 208–2011.
Vancouver
1.
Berton J, Heugebaert T, Debrouwer W, Stevens C. 3-Imidoallenylphophonates: in situ formation and β-alkoxylation. ORGANIC LETTERS. 2016;18(2):208–2011.
MLA
Berton, Jan, Thomas Heugebaert, Wouter Debrouwer, et al. “3-Imidoallenylphophonates: In Situ Formation and Β-alkoxylation.” ORGANIC LETTERS 18.2 (2016): 208–2011. Print.