Advanced search
Add to list

Synthetic entry into 1‑phosphono-3-azabicyclo[3.1.0]hexanes

Wouter Debrouwer (UGent) , Thomas Heugebaert (UGent) , Kristof Van Hecke (UGent) and Christian Stevens (UGent)
(2013) JOURNAL OF ORGANIC CHEMISTRY. 78(17). p.8232-8241
Author
Organization
Abstract
3-Azabicyclo[3.1.0]hex-2-en-1-yl phosphonates were prepared in a five-step reaction route from β-ketophosphonates. The key steps in this sequence are an atom-transfer radical cyclization and an unforeseen lithium−halogen exchange with n-BuLi. The cyclization reaction proceeds with excellent diastereoselectivity. The resulting cyclic imines were reduced, and 3-azabicyclo[3.1.0]hexan-1-yl phosphonates were obtained.
Keywords
EFFICIENT SYNTHESIS, AMINES, PHOSPHONATES, KETONES, 1, 1-BISPHOSPHONO-2-AZA-1, 3-DIENES, CHEMISTRY, AZADIENES, PYRIDINES, ENAMINES, OXIDES

Citation

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

MLA
Debrouwer, Wouter, et al. “Synthetic Entry into 1‑phosphono-3-Azabicyclo[3.1.0]Hexanes.” JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 17, 2013, pp. 8232–41, doi:10.1021/jo401185u.
APA
Debrouwer, W., Heugebaert, T., Van Hecke, K., & Stevens, C. (2013). Synthetic entry into 1‑phosphono-3-azabicyclo[3.1.0]hexanes. JOURNAL OF ORGANIC CHEMISTRY, 78(17), 8232–8241. https://doi.org/10.1021/jo401185u
Chicago author-date
Debrouwer, Wouter, Thomas Heugebaert, Kristof Van Hecke, and Christian Stevens. 2013. “Synthetic Entry into 1‑phosphono-3-Azabicyclo[3.1.0]Hexanes.” JOURNAL OF ORGANIC CHEMISTRY 78 (17): 8232–41. https://doi.org/10.1021/jo401185u.
Chicago author-date (all authors)
Debrouwer, Wouter, Thomas Heugebaert, Kristof Van Hecke, and Christian Stevens. 2013. “Synthetic Entry into 1‑phosphono-3-Azabicyclo[3.1.0]Hexanes.” JOURNAL OF ORGANIC CHEMISTRY 78 (17): 8232–8241. doi:10.1021/jo401185u.
Vancouver
1.
Debrouwer W, Heugebaert T, Van Hecke K, Stevens C. Synthetic entry into 1‑phosphono-3-azabicyclo[3.1.0]hexanes. JOURNAL OF ORGANIC CHEMISTRY. 2013;78(17):8232–41.
IEEE
[1]
W. Debrouwer, T. Heugebaert, K. Van Hecke, and C. Stevens, “Synthetic entry into 1‑phosphono-3-azabicyclo[3.1.0]hexanes,” JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 17, pp. 8232–8241, 2013.
@article{4227463,
  abstract     = {{3-Azabicyclo[3.1.0]hex-2-en-1-yl phosphonates were prepared in a five-step reaction route from β-ketophosphonates. The key steps in this sequence are an atom-transfer radical cyclization and an unforeseen lithium−halogen exchange with n-BuLi. The cyclization reaction proceeds with excellent diastereoselectivity. The resulting cyclic imines were reduced, and 3-azabicyclo[3.1.0]hexan-1-yl phosphonates were obtained.}},
  author       = {{Debrouwer, Wouter and Heugebaert, Thomas and Van Hecke, Kristof and Stevens, Christian}},
  issn         = {{0022-3263}},
  journal      = {{JOURNAL OF ORGANIC CHEMISTRY}},
  keywords     = {{EFFICIENT SYNTHESIS,AMINES,PHOSPHONATES,KETONES,1,1-BISPHOSPHONO-2-AZA-1,3-DIENES,CHEMISTRY,AZADIENES,PYRIDINES,ENAMINES,OXIDES}},
  language     = {{eng}},
  number       = {{17}},
  pages        = {{8232--8241}},
  title        = {{Synthetic entry into 1‑phosphono-3-azabicyclo[3.1.0]hexanes}},
  url          = {{http://dx.doi.org/10.1021/jo401185u}},
  volume       = {{78}},
  year         = {{2013}},
}

Altmetric
View in Altmetric
Web of Science
Times cited: