Modular strategy for the synthesis of functionalized aryl-fused azabicyclo[2.2.2]octanes via sequential Cu/Pd/Ru catalysis.
Aryl-fused 2-azabicyclo[2.2.2]octanes were prepared by a novel sequence of Cu-catalyzed three-component coupling of diversely substituted N-benzyl o-bromoaryl imines with methacryloyl chloride and vinyltributyl stannane followed by Pd-catalyzed Heck annulation. Subsequent diversification of the aryl-fused 2-azabicyclo[2.2.2]octane core was achieved by attaching a flexible linker and a potential second pharmacophore via Ru-catalyzed cross-metathesis and a nucleophilic substitution.
Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Lucas F
LF
McCormick
Helena C
HC
Malinakova
D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
D053961:Azabicyclo Compounds; D010165:Palladium; D003300:Copper; D012428:Ruthenium