Synthetic Entry into 1‑Phosphono-3-azabicyclo[3.1.0]hexanes

Synthetic Entry into 1‑Phosphono-3-azabicyclo[3.1.0]hexanes

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 diastere...

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Veröffentlicht in:Journal of organic chemistry 2013-09, Vol.78 (17), p.8232-8241
Hauptverfasser: Debrouwer, Wouter, Heugebaert, Thomas S. A, Van Hecke, Kristof, Stevens, Christian V
Format: Artikel
Sprache:eng
Schlagworte:
Azabicyclo Compounds - chemical synthesis
Azabicyclo Compounds - chemistry
Cyclization
Molecular Structure
Organophosphonates - chemistry
Phosphorous Acids - chemical synthesis
Phosphorous Acids - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401185u