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Diastereoselective synthesis of (5<i>R</i>,7<i>R</i>)- and (5<i>R</i>,7<i>S</i>)-5,7-dimethyl-6,7-dihydro-5<i>H</i>-dibenz[c,e]azepines

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Published in Synlett. 2000, no. 4, p. 483-486
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 alkylationChiral azepineStille biaryl couplingPalladiumEnantioselective lithiation
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SAUDAN, Lionel, BERNARDINELLI, Gérald Hugues, KUNDIG, Ernst Peter. Diastereoselective synthesis of (5<i>R</i>,7<i>R</i>)- and (5<i>R</i>,7<i>S</i>)-5,7-dimethyl-6,7-dihydro-5<i>H</i>-dibenz[c,e]azepines. In: Synlett, 2000, n° 4, p. 483-486. doi: 10.1055/s-2000-6558 https://archive-ouverte.unige.ch/unige:6200

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Deposited on : 2010-04-20

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