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

Saudan, Lionel; Bernardinelli, Gérald Hugues; Kundig, Ernst Peter

doi:10.1055/s-2000-6558

Scientific article

English

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

ContributorsSaudan, Lionel; Bernardinelli, Gérald Hugues; Kundig, Ernst Peter

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

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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

PID : unige:6200
DOI : 10.1055/s-2000-6558

Journal ISSN0936-5214

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

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