The preparation and alkylation of a butanedione-derived chiral glycine equivalent and its use for the synthesis of α-amino acids and α,α-disubstituted amino acids

Christopher I. Harding, Darren J. Dixon, Steven V. Ley

    Research output: Contribution to journalArticlepeer-review

    Abstract

    A benzyloxycarbonyl protected glycine equivalent 2 has been prepared in enantiopure form and has been used in the synthesis of both α-substituted amino acids and α,α-disubstituted amino acids. The process involved deprotonation to form the corresponding enolates which underwent stereoselective alkylation with various electrophiles and upon hydrolysis gave the corresponding amino acid derivatives as enantiomerically pure products. © 2004 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)7679-7692
    Number of pages13
    JournalTetrahedron
    Volume60
    Issue number35
    DOIs
    Publication statusPublished - 23 Aug 2004

    Keywords

    • Amino acid synthesis
    • Chiral glycine equivalent

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