Skeletal remodelling of α-substituted cyclic eneformamides to α-ketonyl cyclic amines. (4th September 2020)

• Record Type: Journal Article
• Authors: Beng, Timothy K.; Garcia, Jorge; Smith, Meagan; Orellana, Alexis O.
• Is Part Of: New journal of chemistry. Volume 44:Number 36(2020)
• Page Start: 15337
• Page End: 15340
• Publication Date: 2020-09-04
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d0nj02768e
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : A modular dehomologation strategy, which skeletally remodels cyclic α-substituted eneformamides to one-carbon shorter α-ketonyl saturated cyclic amines is described. Abstract : 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(sp 3 )–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.