Skeletal remodelling of α-substituted cyclic eneformamides to α-ketonyl cyclic amines
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A modular dehomologation strategy, which skeletally remodels cyclic α-substituted eneformamides to one-carbon shorter α-ketonyl saturated cyclic amines is described. The approach hinges on N-iodosuccinimide-assisted C–halogen bond formation followed by C–N bond cleavage to arrive at α-iodo ketones, which undergo base-mediated cyclization. An intramolecular C(sp3)–H amination of in situ-generated N-iodo tethered ketones also affords the desired α-ketonyl cyclic amines. The transformation is applicable to an array of α-functionalized eneformamides, but some chemoselective challenges were encountered with a few substrates.
Beng, T. K., Garcia, J., Smith, M., & Orellana, A. O. (2020). Skeletal remodelling of α-substituted cyclic eneformamides to α-ketonyl cyclic amines. New Journal of Chemistry, 44(36), 15337–15340. https://doi.org/10.1039/d0nj02768e
New Journal of Chemistry