title: Dearomatizing Radical Cyclizations and Cyclization Cascades Triggered by Electron-Transfer Reduction of Amide-Type Carbonyls.
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 up to five stereocenters with high diastereocontrol. The first dearomatizing radical cyclizations involving radicals derived from 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.
authors.affiliation: School of Chemistry, Oxford Road, University of Manchester , Manchester, M13 9PL, United Kingdom.
authors.forename: Huan-Ming
authors.identifier: 0000-0001-9461-6508
authors.initials: HM
authors.lastname: Huang
authors.affiliation: School of Chemistry, Oxford Road, University of Manchester , Manchester, M13 9PL, United Kingdom.
authors.forename: David J
authors.identifier: 0000-0003-3179-2509
authors.initials: DJ
authors.lastname: Procter