Dimerization of lithiated terminal aziridines

David M. Hodgson, Steven M. Miles

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Let's get together: Dimerization of enantiopure terminal aziridines by lithiation gives efficiently N-protected 2-ene-1,4-diamines with complete selectivity for the E olefin (see scheme). The usefulness of the method was demonstrated in a concise synthesis of (R,S,S,R)-2,5-diamino-1,6-diphenylhexane- 3,4-diol, the core unit of many extremely potent HIV protease inhibitors and also asymmetric catalysts. (Chemical Equation Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
    Original languageEnglish
    Pages (from-to)935-938
    Number of pages3
    JournalAngewandte Chemie - International Edition
    Volume45
    Issue number6
    DOIs
    Publication statusPublished - 30 Jan 2006

    Keywords

    • Aziridines
    • Lithiation
    • Small ring systems
    • Synthetic methods

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