Enantioselective synthesis of α-fluoro-β 3-amino esters: Synthesis of enantiopure, orthogonally protected α-fluoro- β 3-lysine

Peter Duggan, Martin Johnston, Taryn March

    Research output: Contribution to journalArticle

    20 Citations (Scopus)

    Abstract

    The scope of a tandem conjugate addition-fluorination sequence performed on α,β-unsaturated esters using the enantiopure lithium amide derived from (S)-N-benzyl-N-(α-methylbenzyl)amine, and the electrophilic fluorinating agent N-fluorobenzenesulfonimide has been investigated. Using this method, α-fluoro-β 3-amino esters can be obtained in up to quantitative yield and 80:20 to >99:1 dr. This simple methodology does not rely on the use of α-amino acids from the chiral pool and thus provides the potential for the preparation of enantiopure α-fluoro- β 3-amino acids with a wide variety of side chains. Its utility was demonstrated through the synthesis of orthogonally protected (2S,3S)-α-fluoro-β 3-lysine.

    Original languageEnglish
    Pages (from-to)7365-7372
    Number of pages8
    JournalJournal of Organic Chemistry
    Volume75
    Issue number21
    DOIs
    Publication statusPublished - 5 Nov 2010

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