Stereoselective a-alkylation of fully protected L-serine

Ari M.P. Koskinen, Pauli Saarenketo, Thomas Straub

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    Diastereoselective alkylation of the (2S,4S) and (2R,4S) diastereomers of 3-tert-butyl 4-methyl 2-tert-butyl-1,3-oxazolidine-3,4-dicarboxylate (1a/b) is reported. Formation of both diastereomers of these oxazolidines was achieved by changing
    the order of protection steps, and their relative and absolute configurations were determined by NOESY spectroscopy. The use of the bulky ring substituent tBu together with Boc as the N-protecting group led to the exclusive formation of only one alkylated diastereomer.
    Original languageEnglish
    Pages (from-to)3879-3883
    JournalEuropean Journal of Organic Chemistry
    Publication statusPublished - 2004
    MoE publication typeA1 Journal article-refereed


    • L-serine
    • NOESY
    • stereoselective


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