title: Preparation of tetrasubstituted 3-phosphonopyrroles through hydroamination: scope and limitations.
abstract: Phosphonylated pyrroles were obtained by a ZnCl2-catalyzed 5-exo-dig hydroamination of propargylic enamines. These starting compounds were obtained in two steps from commercially available β-ketophosphonates. The method tolerates a wide variety of substituents at the 1,2- and 5-position of the pyrrole, while further derivatization allows for the introduction of substituents at the 4-position via lithiation or halogenation.
authors.affiliation: SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University , Coupure Links 653, B-9000 Gent, Belgium.
authors.forename: Wouter
authors.initials: W
authors.lastname: Debrouwer
authors.forename: Thomas S A
authors.initials: TS
authors.lastname: Heugebaert
authors.forename: Christian V
authors.initials: CV
authors.lastname: Stevens
mesh_terms: D000586:Amination; D002384:Catalysis; D003500:Cyclization; D054879:Halogenation; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D009943:Organophosphorus Compounds; D011758:Pyrroles