A samarium(II)-mediated, stereoselective cyclization for the synthesis of azaspirocycles

Giuditta Guazzelli, Lorna A. Duffy, David J. Procter

    Research output: Contribution to journalArticlepeer-review

    Abstract

    (Chemical Equation Presented) Unsaturated keto-lactams undergo sequential conjugate reduction-aldol cyclization on treatment with SmI2 to give syn-spirocyclic pyrrolidinones and piperidinones containing vicinal, fully substituted stereocenters with complete diastereocontrol. The substituent on nitrogen and the lactam ring size have a marked impact on the efficiency of the spirocyclization. © 2008 American Chemical Society.
    Original languageEnglish
    Pages (from-to)4291-4294
    Number of pages3
    JournalOrganic Letters
    Volume10
    Issue number19
    DOIs
    Publication statusPublished - 2008

    Keywords

    • ALPHA-PHOSPHONO LACTONES
    • PESTALOTIOPSIN-A
    • FUNCTIONALIZED
    • CYCLOBUTANOLS
    • STEREOCONTROLLED APPROACH
    • 4-EXO-TRIG CYCLIZATION
    • UNSATURATED ALDEHYDES
    • DERIVATIVES
    • REDUCTION
    • IODIDE
    • CORE

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