Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

Jonathan Clayden, Lai Wah Lai, Madeleine Helliwell

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented. © 2004 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)4399-4412
    Number of pages13
    JournalTetrahedron
    Volume60
    Issue number20
    DOIs
    Publication statusPublished - 10 May 2004

    Keywords

    • Atropisomeric amides
    • Ephedrine
    • Imidazolines
    • Oxazolidines

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