title: Synthetic entry into 1-phosphono-3-azabicyclo[3.1.0]hexanes.
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.
authors: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Gent, Belgium.
authors: Wouter
authors: W
authors: Debrouwer
authors: Thomas S A
authors: TS
authors: Heugebaert
authors: Kristof
authors: K
authors: Van Hecke
authors: Christian V
authors: CV
authors: Stevens
mesh_terms: D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D010757:Phosphorous Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D053961:Azabicyclo Compounds; D063065:Organophosphonates; D010757:Phosphorous Acids