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RESEARCH PRODUCT
Stereoselective syntheses of piperidinones and their modification by organometallic coupling reactions
Horst KunzBirgit Krankesubject
Chemistry OrganicMolecular ConformationStereoisomerismCrystallography X-RayMetathesisBiochemistryCoupling reactionStereocenterchemistry.chemical_compoundTransmetalationOrganometallic CompoundsOrganic chemistryMagnesiumPhysical and Theoretical ChemistryPiperidonesGroup 2 organometallic chemistryMolecular StructureChemistryArylOrganic ChemistryStereoisomerismZincModels ChemicalStereoselectivityIminesCopperIodinedescription
Dehydropiperidinones stereoselectively obtained from N-arabinosyl imines were iodinated at the enaminone structure. Knochel iodine-magnesium exchange afforded Grignard compounds of these piperidinone derivatives which reacted, either directly or after transmetalation to zinc or copper intermediates, with alkyl-, aryl- or acylhalides to give correspondingly substituted piperidinones. Stereoselective conjugate allyl cuprate addition to a thus obtained 5-allyl dehydropiperidinone and ring-closing metathesis of the product gave a hydroquinolinone containing three stereogenic centers.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2007-01-06 | Org. Biomol. Chem. |