6533b870fe1ef96bd12cfdeb

RESEARCH PRODUCT

Stereoselective Synthesis of 3-Substituted and 3,4-Disubstituted Piperidine und Piperidin-2-one Derivatives

Horst KunzEllen Klegraf

subject

chemistry.chemical_compoundNucleophilic additionchemistryReagentAmideElectrophileStereoselectivityGeneral ChemistryPiperidineMedicinal chemistry

description

The stereoselective synthesis of 3-substituted and 3,4-disubstituted piperidine and piperidin-2-one derivatives was achieved starting from 2-pyridone. After N-galactosylation and subsequent O-silylation, nucleophilic addition of organometallic reagents proceeded with high regio- and stereoselectivity at 4-position. Substituents at position 3 were stereoselectively introduced by reaction of electrophiles with amide enolates of the N-galactosyl-2-piperidones.

https://doi.org/10.1515/znb-2012-0413