6533b7d8fe1ef96bd12699b9
RESEARCH PRODUCT
Solvent-Enhanced Diastereo- and Regioselectivity in the PdII-Catalyzed Synthesis of Six- and Eight-Membered Heterocycles viacis-Aminopalladation
Reijo SillanpääÁRpád BalázsFerenc FülöpFerenc FülöpAnasztázia HetényiZsolt Szakonyisubject
Vinyl CompoundsCyclohexanecarboxylic AcidsStereochemistrychemistry.chemical_elementPyrimidinonesCatalysisCatalysisCyclohexanesAminationAminationCyclohexylaminesOxidative cyclizationMolecular StructureOrganic ChemistryRegioselectivityStereoisomerismGeneral ChemistryAzocinesAllyl CompoundsSolventchemistryCyclizationIntramolecular forceSolvent effectsOxidation-ReductionPalladiumPalladiumdescription
The Pd(II)-catalyzed intramolecular oxidative cyclization of tosyl-protected cis- and trans-N-allyl-2-aminocyclohexanecarboxamides was examined, and efficient syntheses of cyclohexane-fused pyrimidin-4-ones and 1,5-diazocin-6-ones were developed. In the course of the research, a marked solvent effect was observed on both the regio- and diastereoselectivity. Additionally, a novel Pd(II)-mediated domino oxidation, oxidative amination reaction was discovered. Our experimental and theoretical findings suggest that the reactions proceed via a cis-aminopalladation mechanism.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-06-25 | Chemistry - A European Journal |