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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

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journal contribution
posted on 15.03.2007 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.