title: Synthesis of highly functionalised spiro-indoles by a halogen atom transfer radical cyclization.
abstract: The halogen atom transfer radical cyclization (HATRC) has been evaluated on N-(indolylmethyl)trichloroacetamides under Cu(I)Cl catalysis using nitrogen containing ligands. The ring closure leads to the formation of 3,3-spiro-3H-indoles in moderate to good yields by a 5-exo-mechanism. Derivatives with an N-electron withdrawing substituent also lead to a 5-exo-trig and not to a 6-endo-trig cyclization.
authors.affiliation: Research Group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium. Chris.Stevens@Ugent.be
authors.forename: Christian V
authors.initials: CV
authors.lastname: Stevens
authors.forename: Ellen
authors.initials: E
authors.lastname: Van Meenen
authors.forename: Yves
authors.initials: Y
authors.lastname: Eeckhout
authors.forename: Bart
authors.initials: B
authors.lastname: Vanderhoydonck
authors.forename: Wim
authors.initials: W
authors.lastname: Hooghe
mesh_terms: D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005609:Free Radicals; D007211:Indoles; D008024:Ligands; D013141:Spiro Compounds; D003300:Copper; C028419:cuprous chloride; C029892:cupric chloride