Diastereoselective synthesis of (5R,7R)- and (5R,7S)-5,7-Dimethyl-6,7-dihydro-5H-dibenz[c,e]azepines

Authors:
  • LSLionel A. Saudan
    Lionel A. Saudan
  • GBGérald Bernardinelli
    Gérald Bernardinelli
  • EKE. Peter Kündig
    E. Peter Kündig
Publisher website
Google Scholar
Abstract
Starting from (R)-1-(2-methoxyphenyl)ethylamine, the title compounds were synthesized. Key steps are a diastereoselective imine alkylation and a Pd-catalyzed biaryl coupling. The benzylic stereogenic centers of the (5R,7R)-azepine induce a strong bias for the atropisomeric conformer having aS axial chirality and pseudo equatorial Me groups.