Diastereoselective Synthesis of Aliphatic alpha,alpha-Difluoro-{Beta}3-Amino Esters via a Sonocatalyzed Reformatsky Reaction

Taryn March, Martin Johnston, Peter Duggan

    Research output: Contribution to journalArticle

    21 Citations (Scopus)

    Abstract

    (R)-2-Phenylglycine ethyl ester was found to be a cheap and effective auxiliary for the preparation of aliphatic α,α-difluoro- β 3-amino esters via a Reformatsky reaction performed under sonication conditions. The products were obtained in good to high yield and ≥96:4 dr, thus providing a new stereoselective route to this under-represented class of compounds. A facile one-pot removal of the phenylglycine moiety and concomitant Boc protection subsequently afforded the corresponding Boc-protected β 3-amino esters in excellent yield.

    Original languageEnglish
    Pages (from-to)182-185
    Number of pages4
    JournalOrganic Letters
    Volume14
    Issue number1
    DOIs
    Publication statusPublished - 2012

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