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Scientific article
English

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

Published inSynlett, no. 4, p. 483-486
Publication date2000
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.

Keywords
  • Diastereoselective imine alkylation
  • Chiral azepine
  • Stille biaryl coupling
  • Palladium
  • Enantioselective lithiation
Citation (ISO format)
SAUDAN, Lionel, BERNARDINELLI, Gérald Hugues, KUNDIG, Ernst Peter. Diastereoselective synthesis of (5R,7R)- and (5R,7S)-5,7-Dimethyl-6,7-dihydro-5H-dibenz[c,e]azepines. In: Synlett, 2000, n° 4, p. 483–486. doi: 10.1055/s-2000-6558
Identifiers
ISSN of the journal0936-5214
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Creation04/20/2010 10:09:35 AM
First validation04/20/2010 10:09:35 AM
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