Asymmetric synthesis of enantiomerically enriched atropisomeric amides by desymmetrization of N,N-dialkylmesitamides.

Jonathan Clayden, Paul Johnson, Jennifer H. Pink

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Lithiation and silylation of N,N-dialkylmesitamides using chiral lithium amide bases leads to enantiomerically enriched atropisomeric amides (up to 89% ee) by desymmetrization of the enantiotopic Me groups. [on SciFinder (R)]
    Original languageEnglish
    Pages (from-to)371-375
    JournalJournal of the Chemical Society, Perkin Transactions 1
    DOIs
    Publication statusPublished - 2001

    Keywords

    • Asymmetric synthesis and induction (asym. synthesis of enantiomerically enriched atropisomeric amides by desymmetrization of N,N-dialkylmesitamides); Amides Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of enantiomerically enriched atropisomeric amides by desymmetrization of N,N-dialkylmesitamides); Lithiation; Silylation (regioselective; asym. synthesis of enantiomerically enriched atropisomeric amides by desymmetrization of N,N-dialkylmesitamides)

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