Radical Anions from Urea-type Carbonyls: Radical Cyclizations and Cyclization Cascades

Huanming Huang, Joseph J.W. McDouall, David Procter

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    Abstract

    Radical anions generated from urea carbonyls by reductive electron transfer are exploited in carbon-carbon bond formation. New radical cyclizations of urea radical anions deliver complex nitrogen heterocycles and, depending upon the proton
    source used in the reactions, a chemoselective switch between reaction pathways can deliver two heterobicyclic scaffolds. A computational study has been used to investigate the selectivity of the urea radical processes. Furthermore, radical cyclization cascades involving urea radical anions deliver unusual spirocyclic
    aminal architectures.
    Original languageEnglish
    Pages (from-to)4995-4999
    Number of pages5
    JournalAngewandte Chemie
    Volume57
    Issue number18
    Early online date1 Mar 2018
    DOIs
    Publication statusPublished - 17 Apr 2018

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