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RESEARCH PRODUCT
Palladium-Catalyzed C—C Coupling Reactions in the Enantioselective Synthesis of 2,4-Disubstituted 4,5-Dehydropiperidines Using Galactosylamine as a Stereodifferentiating Auxiliary.
Stephan KnauerHorst Kunzsubject
chemistry.chemical_classificationAldimineStereochemistryHydrideChemistryArylOrganic ChemistryEnantioselective synthesischemistry.chemical_elementGlycosidic bondGeneral MedicineEnolMedicinal chemistryCombinatorial chemistryCatalysisCatalysisInorganic Chemistrychemistry.chemical_compoundC c couplingPiperidinePhysical and Theoretical ChemistryPalladiumdescription
Abstract Stereoselective synthesis of enantiomerically pure 2,4-disubstituted piperidine derivatives, which are considered interesting pharmacophoric structures, was achieved starting with a tandem Mannich–Michael reaction sequence on O -pivaloylated N -galactosyl aldimines. Subsequent conversion of the thus formed 2-substituted dehydropiperidinones into the corresponding enol triflates was carried out by conjugate hydride addition and trapping the enolate with N , N -bis(trifluoromethanesulfonyl)aniline. Their Suzuki–Miyaura coupling with aryl and heteroaryl boronic acids was performed under conditions compatible with the carbohydrate structure, in particular, with the sensitive N -glycosidic bond.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2005-06-21 | ChemInform |