Pyrrolidine-Based Organocatalysts for Enantioselective Michael Addition of Cyclohexanone to trans-beta-Nitrostyrene

Allison P. Carley, Sally Dixon, Jeremy Dunbar Kilburn

    Research output: Contribution to journalArticle

    14 Citations (Scopus)

    Abstract

    A series of readily prepared bifunctional catalysts promote the Michael addition of cyclohexanone to trans-beta-nitrostyrene with excellent asymmetric induction. The enantioselection (up to 97%) and diastereoselection (up to 95:5) is comparable to other pyrrolidine-thiourea organocatalysts recently reported, however, reaction times are often shorter.

    Original languageEnglish
    Pages (from-to)2509-2516
    Number of pages8
    JournalSynthesis
    Issue number15
    DOIs
    Publication statusPublished - 3 Aug 2009

    Keywords

    • addition reactions
    • asymmetric catalysis
    • Michael additions
    • bifunctional catalysis
    • nitroolefin
    • PRIMARY AMINE-THIOUREA
    • BIFUNCTIONAL ORGANOCATALYSTS
    • CONJUGATE ADDITION
    • NITRO-MICHAEL
    • PROTECTING GROUP
    • ALDOL REACTIONS
    • NITROOLEFINS
    • KETONES
    • PROLINE
    • DERIVATIVES

    Cite this

    Pyrrolidine-Based Organocatalysts for Enantioselective Michael Addition of Cyclohexanone to trans-beta-Nitrostyrene. / Carley, Allison P.; Dixon, Sally; Kilburn, Jeremy Dunbar.

    In: Synthesis, No. 15, 03.08.2009, p. 2509-2516.

    Research output: Contribution to journalArticle

    Carley, Allison P. ; Dixon, Sally ; Kilburn, Jeremy Dunbar. / Pyrrolidine-Based Organocatalysts for Enantioselective Michael Addition of Cyclohexanone to trans-beta-Nitrostyrene. In: Synthesis. 2009 ; No. 15. pp. 2509-2516.
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