3 years ago

Radical Heterocyclization and Heterocyclization Cascades Triggered by Electron Transfer to Amide-Type Carbonyl Compounds

Radical Heterocyclization and Heterocyclization Cascades Triggered by Electron Transfer to Amide-Type Carbonyl Compounds
Huan-Ming Huang, David J. Procter
Radical heterocyclizations triggered by electron transfer to amide-type carbonyls, using SmI2-H2O, provide straightforward access to bicyclic heterocyclic scaffolds containing bridgehead nitrogen centers. Furthermore, the first radical heterocyclization cascade triggered by reduction of amide-type carbonyls delivers novel, complex tetracyclic architectures containing five contiguous stereocenters with excellent diastereocontrol. Building bridges: Radical heterocyclization and heterocyclization cascades triggered by electron transfer to amide-type carbonyl groups provide straightforward access to heterocyclic scaffolds containing bridgehead nitrogen atoms. The radical cascade cyclizations deliver novel tetracyclic architectures, containing five contiguous stereocenters, with excellent diastereocontrol.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708354

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