Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of α-hydroxy-γ-amino acid derivatives

Darren J. Dixon, Steven V. Ley, Félix Rodríguez

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Figure presented The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block undergoes efficient and highly diastereoselective lithium enolate Michael additions to α,β-unsaturated ketones, lactones, and nitro olefins. Subsequent deprotection of these Michael adducts gives α-hydroxy acids in very high yield. Hydrogenation of the nitro group in some of the adducts leads to γ-lactams, which can be easily converted into α-hydroxy-γ-amino acid derivatives.
    Original languageEnglish
    Pages (from-to)3753-3755
    Number of pages2
    JournalOrganic Letters
    Volume3
    Issue number23
    DOIs
    Publication statusPublished - 15 Nov 2001

    Keywords

    • Stereoselective synthesis (diastereoselective Michael addn. of butanediacetal desymmetrized glycolic acid to a,b-unsatd. ketones, lactones, and nitro olefins and prepn. of a-hydroxy-g-amino acid derivs.); Michael reaction (stereoselective; diastereoselective Michael addn. of butanediacetal desymmetrized glycolic acid to a,b-unsatd. ketones, lactones, and nitro olefins and prepn. of a-hydroxy-g-amino acid derivs.)

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