title: Novel synthesis of azepine derivatives via copper-mediated cyclization of 2-aza-hepta-2,4-dien-6-ynyl anions. Intramolecular addition of organocopper centers to the C-C triple bond.
abstract: Deprotonation of alkynyl imines 1 with LDA at low temperature and subsequent transmetalation with copper thiophenolate gives the annulated azepines 11a-i in 41-73% yield after aqueous workup. The key step of the reaction is a copper-mediated intramolecular nucleophilic attack at the triple bond. [reaction: see text]
authors.affiliation: Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, D-48149 Münster, Germany.
authors.forename: Volodymyr
authors.initials: V
authors.lastname: Lyaskovskyy
authors.forename: Klaus
authors.initials: K
authors.lastname: Bergander
authors.forename: Roland
authors.initials: R
authors.lastname: Fröhlich
authors.forename: Ernst-Ulrich
authors.initials: EU
authors.lastname: Würthwein
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000838:Anions; D001381:Azepines / Q000138:chemical synthesis*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D009942:Organometallic Compounds / Q000737:chemistry*; D011522:Protons; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000838:Anions; D001381:Azepines; D009942:Organometallic Compounds; D011522:Protons; D002244:Carbon; D003300:Copper