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3-Imidoallenylphophonates: in situ formation and β-alkoxylation

Jan Berton (UGent) , Thomas Heugebaert (UGent) , Wouter Debrouwer (UGent) and Christian Stevens (UGent)
(2016) ORGANIC LETTERS. 18(2). p.208-2011
Author
Organization
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.
Keywords
PHOSPHITES, AMINO ALLENEPHOSPHONATES, ALCOHOLS, ALKYNES, (DIMETHYLAMINO)ALLENE, HYDROAMINATION, REARRANGEMENT, NUCLEOPHILES, ALLENAMIDES, CYCLIZATION

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Citation

Please use this url to cite or link to this publication:

MLA
Berton, Jan et al. “3-Imidoallenylphophonates: In Situ Formation and Β-alkoxylation.” ORGANIC LETTERS 18.2 (2016): 208–2011. Print.
APA
Berton, J., Heugebaert, T., Debrouwer, W., & Stevens, C. (2016). 3-Imidoallenylphophonates: in situ formation and β-alkoxylation. ORGANIC LETTERS, 18(2), 208–2011.
Chicago author-date
Berton, Jan, Thomas Heugebaert, Wouter Debrouwer, and Christian Stevens. 2016. “3-Imidoallenylphophonates: In Situ Formation and Β-alkoxylation.” Organic Letters 18 (2): 208–2011.
Chicago author-date (all authors)
Berton, Jan, Thomas Heugebaert, Wouter Debrouwer, and Christian Stevens. 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.
IEEE
[1]
J. Berton, T. Heugebaert, W. Debrouwer, and C. Stevens, “3-Imidoallenylphophonates: in situ formation and β-alkoxylation,” ORGANIC LETTERS, vol. 18, no. 2, pp. 208–2011, 2016.
@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},
  keywords     = {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 β-alkoxylation},
  url          = {http://dx.doi.org/10.1021/acs.orglett.5b03314},
  volume       = {18},
  year         = {2016},
}

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