ol063081y_si_001.pdf (70.73 kB)

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

Download (70.73 kB)
journal contribution
posted on 15.03.2007, 00:00 by Volodymyr Lyaskovskyy, Klaus Bergander, Roland Fröhlich, Ernst-Ulrich Würthwein
Deprotonation of alkynyl imines 1 with LDA at low temperature and subsequent transmetalation with copper thiophenolate gives the annulated azepines 11ai in 41−73% yield after aqueous workup. The key step of the reaction is a copper-mediated intramolecular nucleophilic attack at the triple bond.