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Synlett 2000; 2000(4): 483-486
DOI: 10.1055/s-2000-6558
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Diastereoselective synthesis of (5R,7R)- and (5R,7S)-5,7-Dimethyl-6,7-dihydro-5H-dibenz[c,e]azepines

Lionel A. Saudan* , Gérald Bernardinelli, E. Peter Kündig
  • *Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland; Fax (+41 22) 3 28 73 96; E-mail: Peter.Kundig@chiorg.unige.ch
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Publication History

Publication Date:
31 December 2000 (online)

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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.

diastereoselective imine alkylation - chiral azepine - Stille biaryl coupling - palladium - enantioselective lithiation