Enantioselective route to 5-methyl-And 5,7-dimethyl-6,7-dihydro-sh- dibenz[c,e]azepine: Secondary amines with switchable axial chirality

Silvain L. Pira, Timothy W. Wallace, Jonathan P. Graham

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    Abstract

    (-) -5-Methyl-6, 7-dihydro-5H-dibenz[c, e]azepine 4, a new secondary amine featuring an axis-center stereochemical relay, was prepared enantioselectively from 2'-acetylbiphenyl-2-carboxylic acid, using (R) -2-phenylglycinol as an auxiliary for the control of both elements of chirality. The biaryl axis in 4 preferentially adopts the aS-configuration, with the methyl substituent pseudoequatorial, but conversion into the corresponding N-Boc derivative locks the axis into the aR-configuration, as predicted on the basis of molecular mechanics calculations. © 2009 American Chemical Society.
    Original languageEnglish
    Pages (from-to)1663-1666
    Number of pages3
    JournalOrganic Letters
    Volume11
    Issue number7
    DOIs
    Publication statusPublished - 2 Apr 2009

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