Ring-opening and -expansion of 2,2′-biaziridine: Access to diverse enantiopure linear and bicyclic vicinal diamines

Stephen J. Bailey, Steven M. Wales, Anthony C. Willis, Paul A. Keller*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    22 Citations (Scopus)

    Abstract

    The chiral pool-derived 1,1′-ditosyl-2,2′-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2′-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.

    Original languageEnglish
    Pages (from-to)4344-4347
    Number of pages4
    JournalOrganic Letters
    Volume16
    Issue number16
    DOIs
    Publication statusPublished - 15 Aug 2014

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