Dearomatizing radical cyclizations and cyclization cascades triggered by electron-transfer reduction of amide-type car-bonyls

Huan-Ming Huang, David Procter

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    Abstract

    Highly selective dearomatizing radical cyclizations and cyclization cascades, triggered by single electron-transfer to amide-type carbonyls by SmI2-H2O-LiBr provide efficient access to unprecedented spirocyclic scaffolds containing five stereocenters with high diastereocontrol. The first dearomatizing radical cyclizations involving radicals derived from the amide carbonyls by single electron-transfer take place under mild conditions and engage a range of aromatic and heteroaromatic systems present in the barbiturate substrates. The radical cyclizations deliver new polycyclic hemiaminals or enamines selectively, depending on the conditions employed, that are based on a medicinally proven scaffold and can be readily manipulated.
    Original languageEnglish
    JournalJournal of the American Chemical Society
    Volume139
    Issue number4
    Early online date20 Dec 2016
    DOIs
    Publication statusPublished - 2017

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