Download PDF
Synlett 2000; 2000(4): 483-486
DOI: 10.1055/s-2000-6558
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >